Aromatic diamide derivatives or salts thereof, agricultural/horticultural chemicals and method of using the same

ABSTRACT

Aromatic diamide derivative represented by the general formula (I) or a salt thereof and agricultural/herticultural composition containing the same as the active ingredient, 
                 
 
wherein A 1  represents alkylene, alkenylene or alkynylene; B represents, CO— or —C(═N—OR 4 )— (wherein R 4  represents H, etc.); R 1  to R 3  represent each H, etc.; Q 1  to Q 5  represent each N or carbon; Y represents halogeno, etc.; m is from 0 to 5; and Z 1  and Z 2  represent each O or S.

This application is the national phase of international application PCT/JP00/06514 filed 22 Sep. 2000 which designated the U.S.

TECHNICAL FIELD

The present invention relates to an aromatic diamide derivative or a salt thereof; an agrohorticultural composition, particularly an agrohorticultural insecticide both containing the derivative or the salt as an effective ingredient; and a method for using the same.

BACKGROUND ART

A compound similar to the aromatic diamide derivative represented by the general formula (I) of the present invention is disclosed in EP 919542 A2.

DISCLOSURE OF THE INVENTION

The present inventors made an intensive study in order to develop a novel agrohorticultural composition, particularly an agrohorticultural insecticide and, as a result, found out that an aromatic diamide derivative represented by the general formula (I) or a salt thereof according to the present invention is a novel compound not described in any literature and is useful as an agrohorticultural composition, particularly as an agrohorticultural insecticide. The present invention has been completed based on the above finding.

The present invention relates to an aromatic diamide derivative represented by the following general formula (I) or a salt thereof; an agrohorticultural composition, particularly an agrohorticultural insecticide; and a method for using the insecticide:

{wherein A¹ is a (C₁-C₈)alkylene group; a substituted (C₁-C₈) alkylene group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, (C₁-C₆)alkylthio(C₁-C₆)alkyl groups, (C₁-C₆)alkoxycarbonyl groups and phenyl group; a (C₃-C₈)alkenylene group; a substituted (C₃-C₈)alkenylene group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, (C₁-C₆)-alkylthio(C₁-C₆)alkyl groups, (C₁-C₆)alkoxycarbonyl groups and phenyl group; a (C₃-C₈)alkynylene group; or a substituted (C₃-C₈)alkynylene group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups. (C₁-C₆)alkylsulfinyl groups, halo (C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, (C₁-C₆)alkylthio(C₁-C₆)alkyl groups, (C₁-C₆)alkoxycarbonyl groups and phenyl group;

-   -   in the (C₁-C₈)alkylene group, the substituted (C₁-C₈) alkylene         group, the (C₃-C₈)alkenylene group, the substituted (C₃-C₈)         alkenylene group, the (C₃-C₈)-alkynylene group or the         substituted (C₃-C₈)alkynylene group, any saturated carbon atom         may be substituted with a (C₂-C₅) alkylene group to form a         (C₃-C₆)cycloalkane ring; further in the (C₁-C₈)alkylene group,         the substituted (C₂-C₅) alkylene group, the (C₃-C₈)alkenylene         group or the substituted (C₃-C₈) alkenylene group, any two         carbon atoms may be combined with an alkylene group or an         alkenylene group to form a (C₃-C₆)cycloalkane ring or a         (C₃-C₆)cycloalkene ring;     -   B is —CO— or —C(═N—OR⁴)— (wherein R⁴ is a hydrogen atom; a         (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl         group; a halo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynyl group; a         (C₃-C₆)cycloalkyl group; a phenyl(C₁-C₄)alkyl group; or a         substituted phenyl(C₁-C₄)alkyl group having, on the ring, one or         more same or different substituents selected from halogen atoms,         cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl         groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups);     -   R₁ is a hydrogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl         group; a (C₂-C₆)alkenyl group; a halo(C₂-C₆)alkenyl group; a         (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a         (C₁-C₆)alkoxy group; a halo(C₁-C₆)alkoxy group; a         (C₁-C₆)alkylthio group; a halo(C₁-C₆)alkylthio group; a         mono(C₁-C₆)alkylamino group; a di(C₁-C₆)alkylamino group wherein         the two alkyl groups may be the same or different; a phenyl         group; a substituted phenyl group having one or more same or         different substituents selected from halogen atoms, cyano group,         nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,         (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio         groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl         groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl         groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino         groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups         may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups;         a phenylamino group; a substituted phenylamino group having, on         the ring, one or more same or different substituents selected         from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl         groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups,         halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,         halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,         halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups,         halo (C₁-C₆) alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups,         di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be         the same or different, and (C₁-C₆)alkoxycarbonyl groups; a         phenyloxy group; a substituted phenyloxy group having one or         more same or different substituents selected from halogen atoms,         cyano groups, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl         groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)-alkoxycarbonyl groups; a phenylthio group; a substituted         phenylthio group having one or more same or different         substituents selected from halogen atoms, cyano group, nitro         group, (C₁-C₆)alkyl groups, halo (C₁-C₆)alkyl groups,         (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio         groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl         groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl         groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino         groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups         may be the same or different, and (C₁-C₆)alkoxycarbonyl groups;         a heterocyclic group; or a substituted heterocyclic group having         one or more same or different substituents selected from halogen         atoms, cyano group, nitro group, (C₁-C₆)alkyl groups,         halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy         groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and (C₁-C₆)—         alkoxycarbonyl groups;     -   R¹ may bond with A′ to form a 4- to 7-membered ring which may         contain, as a ring-constituting atom(s), one or two same or         different atoms selected from oxygen, sulfur and nitrogen atoms;     -   R² and R³ may be the same or different and are each a hydrogen         atom, a (C₃-C₆)cycloalkyl group or —A²—R⁵ [wherein A² is         —C(═O)—, —C(═S)—, —C(═NR⁶)— (wherein R⁶ is a hydrogen atom; a         (C₁-C₆)alkyl group; a (C₁-C₆)alkoxy group; a         mono(C₁-C₆)alkylamino group; a di(C₁-C₆)-alkylamino group         wherein the two alkyl groups may be the same or different; a         (C₁-C₆)alkoxycarbonyl group; a phenyl group; or a substituted         phenyl group having one or more same or different substituents         selected from halogen atoms, cyano group, nitro group,         (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy         groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,         halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,         halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups,         halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups,         di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be         the same or different, and (C₁-C₆)alkoxycarbonyl groups), a         (C₁-C₈)alkylene group, a halo(C₁-C₈)alkylene group, a         (C₃-C₆)alkenylene group, a halo(C₃-C₆)alkenylene group, a         (C₃-C₆)alkynylene group or a halo(C₃-C₆)alkynylene group;     -   (1) when A² is —C(═O)—, —C(═S)— or —C(═NR⁶)— (wherein R⁶ has the         same definition as given above), R⁵ is a hydrogen atom; a         (C₁-C₆)alkyl group; a halo(C₁-C₆)-alkyl group; a (C₁-C₆)alkoxy         group; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group;         a phenyl group; a substituted phenyl group having one or more         same or different substituents selected from halogen atoms,         cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl         groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)-alkoxycarbonyl groups; a heterocyclic group; a         substituted heterocyclic group having one or more same or         different substituents selected from halogen atoms, cyano group,         nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,         (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio         groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl         groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl         groups, if halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)-alkoxycarbonyl groups; or —A³—R⁷ (wherein A³ is —O—, —S—         or —N(R⁸)— (wherein R⁸ is a hydrogen atom; a         (C₁-C₆)-alkylcarbonyl group; a halo(C₁-C₆)alkylcarbonyl group; a         (C₁-C₆)alkoxycarbonyl group; a phenylcarbonyl group; a         substituted phenylcarbonyl group having one or more same or         different substituents selected from halogen atoms, cyano group,         nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,         (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio         groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl         groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl         groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)-alkylamino         groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups         may be the same or different, and (C₁-C₆) alkoxycarbonyl groups;         a phenyl (C₁-C₄)-alkoxycarbonyl group; or a substituted         phenyl(C₁-C₄)-alkoxycarbonyl group having, on the ring, one or         more same or different substituents selected from halogen atoms,         cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl         groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)-alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)-alkylamino groups, di(C₁-C₆)alkylamino groups         wherein the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups); and R⁷ is a (C₁-C₆)alkyl group; a         halo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl group; a         halo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynyl group; a         halo(C₃-C₆)alkynyl group; a (C₃-C₆)cycloalkyl group; a         halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkylcarbonyl group; a         halo(C₁-C₆)alkylcarbonyl group; a (C₁-C₆)-alkoxycarbonyl group;         a phenyl group; a substituted phenyl group having one or more         same or different substituents selected from halogen atoms,         cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl         groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)-alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups; a phenyl(C₁-C₄)alkyl group; a         substituted phenyl(C₁-C₄)alkyl group having, on the ring, one or         more same or different substituents selected from halogen atoms,         cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl         groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁         -C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo (C₁-C₆) alkylsulfonyl groups,         mono (C₁-C₆)-alkylamino groups, di(C₁-C₆)alkylamino groups         wherein the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; or a         substituted heterocyclic group having one or more same or         different substituents selected from halogen atoms, cyano group,         nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,         (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio         groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl         groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl         groups, halo(C₁-C₆) alkylsulfonyl groups, mono(C₁-C₆) alkylamino         groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups         may be the same or different, and (C₁-C₆)-alkoxycarbonyl         groups);     -   (2) when A² is a (C₁-C₈)alkylene group, a halo(C₁-C₈)alkylene         group, a (C₃-C₆)alkenylene group, a halo(C₁-C₆)alkenylene group,         a (C₃-C₆)alkynylene group or a halo(C₃-C₆)alkynylene group, R⁵         is a hydrogen atom; a halogen atom; a cyano group; a nitro         group; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group;         a (C₁-C₆)alkoxycarbonyl group; a phenyl group; a substituted         phenyl group having one or more same or different substituents         selected from halogen atoms, cyano group, nitro group,         (C₁-C₆)alkyl groups, halo(C₁-C₆) alkyl groups, (C₁-C₆) alkoxy         groups, halo (C₁-C₆) alkoxy groups, (C₁-C₆)alkylthio groups,         halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,         halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups,         halo(C₁-C₆)alkylsulfonyl groups, mono (C₁-C₆) alkylamino groups,         di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be         the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a         heterocyclic group; a substituted heterocyclic group having one         or more same or different substituents selected from halogen         atoms, cyano group, nitro group, (C₁-C₆)alkyl groups,         halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy         groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)-alkoxycarbonyl groups; or —A⁴—R⁹ (wherein A⁴ is —O—,         —S—, —SO—, —SO₂—, —N(R⁸)— (R⁸ has the same definition as given         above), —C(═O)— or —C(═NOR⁴)— (R⁴ has the same definition as         given above);     -   (i) when A⁴ is —O—, —S—, —SO—, —SO₂— or —N(R⁸)—(R⁸ has the same         definition as given above), R⁹ is a hydrogen atom; a         (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl         group; a halo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynyl group; a         halo(C₃-C₆)alkynyl group; a (C₃-C₆)cycloalkyl group; a         halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkylcarbonyl group; a         halo(C₁-C₆)-alkylcarbonyl group; a (C₁-C₆)alkoxycarbonyl group;         a phenyl group; a substituted phenyl group having one or more         same or different substituents selected from halogen atoms,         cyano group, nitro group, (C₁-C₆)alkyl groups, halo (C₁-C₆)         alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)-alkylamino groups, di(C₁-C₆)alkylamino groups         wherein the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups; a phenyl(C₁-C₄)alkyl group; a         substituted phenyl(C₁-C₄)alkyl group having, on the ring, one or         more same or different substituents selected from halogen atoms,         cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl         groups, (C₁-C₆)-alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)-alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; or a         substituted heterocyclic group having one or more same or         different substituents selected from halogen atoms, cyano group,         nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,         (C₁-C₆)-alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)-alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups;     -   (ii) when A⁴ is —C(═O)— or —C(═N—OR⁴)— (R⁴ has the same         definition as given above), R⁹ is a hydrogen atom; a         (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₂-C₆)alkenyl         group; a halo(C₂-C₆)alkenyl group; a (C₃-C₆)cycloalkyl group; a         halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxy group; a         halo(C₁-C₆)alkoxy group; a (C₁-C₆)alkylthio group; a         halo(C₁-C₆)alkylthio group; a mono(C₁-C₆)alkylamino group; a         di(C₁-C₆)alkylamino group wherein the two alkyl groups may be         the same or different; a phenyl group; a substituted phenyl         group having one or more same or different substituents selected         from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl         groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)-alkoxy groups,         halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,         halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,         halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)-alkylsulfonyl groups,         halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups,         di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be         the same or different, and (C₁-C₆)alkoxycarbonyl groups; a         phenylamino group; a substituted phenylamino group having, on         the ring, one or more same or different substituents selected         from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl         groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups,         halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,         halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,         halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups,         halo(C₁-C₆)-alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups,         di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be         the same or different, and (C₁-C₆)alkoxycarbonyl groups; a         phenyloxy group; a substituted phenyloxy group having one or         more same or different substituents selected from halogen atoms,         cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl         groups, (C₁-C₆)-alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)-alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups; a phenylthio group; a substituted         phenylthio group having, on the ring, one or more same or         different substituents selected from halogen atoms, cyano group,         nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,         (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio         groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl         groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl         groups, halo(C₁-C₆)-alkylsulfonyl groups, mono(C₁-C₆)alkylamino         groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups         may be the same or different, and (C₁-C₆)alkoxycarbonyl groups;         a heterocyclic group; or a substituted heterocyclic group having         one or more same or different substituents selected from halogen         atoms, cyano group, nitro group, (C₁-C₆)alkyl groups,         halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy         groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)-alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups)];     -   R² may bond with A¹ or R¹ to form a 4- to 7-membered ring which         may contain, as a ring-constituting atom(s), one or two same or         different atoms selected from oxygen, sulfur and nitrogen atoms;     -   Q₁ to Q₄ may be the same or different and are each a nitrogen         atom or a carbon atom which may be substituted with X, and X may         be the same or different, and is a halogen atom; a cyano group;         a nitro group; a (C₃-C₆)cycloalkyl group; a         halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxycarbonyl group; a         phenyl group; a substituted phenyl group having one or more same         or different substituents selected from halogen atoms, cyano         group, nitro group, (C₁-C₆)alkyl groups, halo (C₁-C₆)alkyl         groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)-alkoxycarbonyl groups; a heterocyclic group; a         substituted heterocyclic group having one or more same or         different substituents selected from halogen atoms, cyano group,         nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,         (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio         groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl         groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl         groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino         groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups         may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups;         or —A⁵—R¹⁰ [wherein A⁵ is —O—, —S—, —SO—, —SO₂—, —C(═O)—,         —C(═NOR⁴)— (R⁴ has the same definition as given above), a         (C₁-C₆)alkylene group, a halo(C₁-C₆)alkylene group, a         (C₂-C₆)alkenylene group, a halo(C₂-C₆)alkenylene group, a         (C₂-C₆)alkynylene group or a halo(C₂-C₆)alkynylene group;     -   (1) when A⁵ is —O—, —S—, —SO— or —SO₂—, R¹⁰ is a         halo(C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkenyl group; a         phenyl group; a substituted phenyl group having one or more same         or different substituents selected from halogen atoms, cyano         group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl         groups, (C₁-C₆)-alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)-alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; a         substituted heterocyclic group having one or more same or         different substituents selected from halogen atoms, cyano group,         nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,         (C₁-C₆)-alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)-alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups; or —A⁶—R¹¹(wherein A⁶ is a         (C₁-C₆)alkylene group, a halo(C₁-C₆)-alkylene group, a         (C₃-C₆)alkenylene group, a halo(C₃-C₆)alkenylene group, a         (C₃-C₆)alkynylene group or a halo(C₃-C₆)alkynylene group, and         R¹¹ is a hydrogen atom; a halogen atom; a (C₃-C₆)cycloalkyl         group; a halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxycarbonyl         group; a phenyl group; a substituted phenyl group having one or         more same or different substituents selected from halogen atoms,         cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl         groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)-alkylamino groups, di(C₁-C₆)alkylamino groups         wherein the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups; or —A⁷—R¹² (wherein A⁷ is —O—,         —S—, —SO— or —SO₂—, and R¹² is a (C₁-C₆)alkyl group; a         halo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl group; a         halo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynyl group; a         halo(C₃-C₆)alkynyl group; a (C₃-C₆)cycloalkyl group; a         halo(C₃-C₆)cycloalkyl group; a phenyl group; a substituted         phenyl group having one or more same or different substituents         selected from halogen atoms, cyano group, nitro group,         (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy         groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,         halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,         halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups,         halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups,         di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be         the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a         heterocyclic group; or a substituted heterocyclic group having         one or more same or different substituents selected from halogen         atoms, cyano group, nitro group, (C₁-C₆)alkyl groups,         halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy         groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)-alkoxycarbonyl groups));     -   (2) when A⁵ is —C(═O)— or —C(═NOR⁴)—(R⁴ has the same definition         as given above), R¹⁰ is a (C₁-C₆)-alkyl group; a         halo(C₁-C₆)alkyl group; a (C₂-C₆)alkenyl group; a         halo(C₂-C₆)alkenyl group; a (C₃-C₆)cycloalkyl group; a         halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxy group; a         (C₁-C₆)alkylthio group; a mono(C₁-C₆)alkylamino group; a         di(C₁-C₆)alkylamino group wherein the two alkyl groups may be         the same or different; a phenyl group; a substituted phenyl         group having one or more same or different substituents selected         from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl         groups, halo(C₁-C₆) alkyl groups, (C₁-C₆) alkoxy groups, halo         (C₁-C₆) alkoxy groups, (C₁-C₆)alkylthio groups,         halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,         halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups,         halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups,         di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be         the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a         phenylamino group; a substituted phenylamino group having, on         the ring, one or more same or different substituents selected         from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl         groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups,         halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,         halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,         halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups,         halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)-alkylamino groups,         di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be         the same or different, and (C₁-C₆)alkoxycarbonyl groups; a         heterocyclic group; or a substituted heterocyclic group having         one or more same or different substituents selected from halogen         atoms, cyano group, nitro group, (C₁-C₆)alkyl groups,         halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy         groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)-alkoxycarbonyl groups;     -   (3) when A⁵ is a (C₁-C₆)alkylene group, a halo(C₁-C₆)alkylene         group, a (C₂-C₆)alkenylene group, a halo(C₂-C₆)alkenylene group,         a (C₂-C₆)alkynylene group or a halo(C₂-C₆)alkynylene group, R¹⁰         is a hydrogen atom; a halogen atom; a (C₃-C₆)cycloalkyl group; a         halo(C₃-C₆)-cycloalkyl group; a (C₁-C₆)alkoxycarbonyl group; a         phenyl group; a substituted phenyl group having one or more same         or different substituents selected from halogen atoms, cyano         group, nitro group, (C₁-C₆)alkyl groups, halo (C₁-C₆) alkyl         groups, (C₁-C₆) alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo (C₁ -C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)-alkylamino groups, di(C₁-C₆)alkylamino groups         wherein the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; a         substituted heterocyclic group having one or more same or         different substituents selected from halogen atoms, cyano group,         nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,         (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio         groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl         groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl         groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino         groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups         may be the same or different, and (C₁-C₆)— alkoxycarbonyl         groups; or —A⁸—R¹³ (wherein A⁸ is —O—, —S—, —SO— or —SO₂—, and         R¹³ is a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group;         a phenyl group; a substituted phenyl group having one or more         same or different substituents selected from halogen atoms,         cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl         groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)-alkoxycarbonyl groups; a heterocyclic group; a         substituted heterocyclic group having one or more same or         different substituents selected from halogen atoms, cyano group,         nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,         (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy, groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)-alkoxycarbonyl groups; or —A⁹—R¹⁴ (wherein A⁹ is a         (C₁-C₆)alkylene group, a halo(C₁-C₆)alkylene group, a         (C₂-C₆)alkenylene group, a halo(C₂-C₆)alkenylene group, a         (C₂-C₆) alkynylene group or a halo (C₃-C₅) alkynylene group, and         R¹⁴ is a hydrogen atom; a halogen atom; a (C₃-C₆)-cycloalkyl         group; a halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxy group; a         halo (C₁-C₆) alkoxy group; a (C₁-C₆)alkylthio group; a         halo(C₁-C₆)alkylthio group; a (C₁-C₆)alkylsulfinyl group; a         halo(C₁-C₆)alkylsulfinyl group; a (C₁-C₆)alkylsulfonyl group; a         halo(C₁-C₆)alkylsulfonyl group; a phenyl group; a substituted         phenyl group having one or more same or different substituents         selected from halogen atoms, cyano group, nitro group,         (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy         groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,         halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,         halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups,         halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups,         di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be         the same or different, and (C₁-C₆)alkoxycarbonyl groups; a         phenyloxy group; a substituted phenyloxy group having one or         more same or different substituents selected from halogen atoms,         cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl         groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups,         (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups; a phenylthio group; a substituted         phenylthio group having one or more same or different         substituents selected from halogen atoms, cyano group, nitro         group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,         (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio         groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl         groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl         groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino         groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups         may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups;         a heterocyclic group; or a substituted heterocyclic group having         one or more same or different substituents selected from halogen         atoms, cyano group, nitro group, (C₁-C₆) alkyl groups, halo         (C₁-C₆) alkyl groups, (C₁-C₆) alkoxy groups, halo (C₁-C₆) alkoxy         groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)-alkoxycarbonyl groups))];     -   the two Xs bonding to the adjacent two carbon atoms constituting         the aromatic ring containing Q¹ to Q⁴ may bond to each other to         form a condensed ring; the condensed ring may have one or more         same or different substituents selected from halogen atoms,         cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl         groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)         alkylthio groups, halo (C₁-C₆) alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)-alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups;     -   Qs is a nitrogen atom or a carbon atom;     -   Y may be the same or different, and is a halogen atom; a cyano         group; a nitro group; a halo(C₃-C₆)cycloalkyl group; a phenyl         group; a substituted phenyl group having one or more same or         different substituents selected from halogen atoms, cyano group,         nitro group, (C₁-C₆) alkyl groups, halo (C₁-C₆) alkyl groups,         (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)         alkylthio groups, halo (C₁-C₆) alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; a         substituted heterocyclic group having one or more same or         different substituents selected from halogen atoms, cyano group,         nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups,         (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)         alkylthio groups, halo (C₁-C₆) alkylthio groups,         (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups,         (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)-alkylsulfonyl groups,         mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein         the two alkyl groups may be the same or different, and         (C₁-C₆)alkoxycarbonyl groups; or —A⁵—R¹⁰ (A⁵ and R¹⁰ each have         the same definition as given above);     -   the two Ys bonding to the adjacent two carbon atoms constituting         the aromatic ring containing Q⁵ may bond to each other to form a         condensed ring; the condensed ring may have one or more same or         different substituents selected from halogen atoms, (C₁-C₆)alkyl         groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups,         halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,         halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo         (C—C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups,         halo(C₁-C₆)alkylsulfonyl groups, phenyl group, substituted         phenyl groups having one or more same or different substituents         selected from halogen atoms, cyano group, nitro group,         (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy         groups, halo(C₁-C₆) alkoxy groups, (C₁-C₆)alkylthio groups,         halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,         halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups,         halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups,         di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be         the same or different, and (C₁-C₆)-alkoxycarbonyl groups,         heterocyclic groups, and substituted heterocyclic groups having         one or more same or different substituents selected from halogen         atoms, cyano group, nitro group, (C₁-C₆)alkyl groups,         halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo         (C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups,         halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups,         halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups,         halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups,         di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be         the same or different, and (C₁-C₆)-alkoxycarbonyl groups;     -   m is an integer of 0 to 5;     -   Z¹ and Z² may be the same or different and are each an oxygen         atom or a sulfur atom}.

MODE FOR CARRYING OUT THE INVENTION

In the definition of the aromatic diamide derivative represented by the general formula (I) or the salt thereof according to the present invention, “halogen atom” refers to chlorine atom, bromine atom, iodine atom or fluorine atom; “(C₁-C₆)alkyl group” refers to a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl or the like; “halo(C₁-C₆)alkyl group” refers to a straight chain or branched chain alkyl group having 1 to 6 carbon atoms, substituted with one or more same or different halogen atoms; “(C₁-C₈)alkylene group” refers to a straight chain or branched chain alkylene group having 1 to 8 carbon atoms, such as methylene, ethylene, propylene, trimethylene, dimethylmethylene, tetramethylene, isobutylene, dimethylethylene, octamethylene or the like.

-   -   “(C₃-C₆)cycloalkyl group” refers to an alicyclic alkyl group         having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl,         cyclopentyl, cyclohexyl or the like.     -   “The 4- to 7-membered ring which may contain one or two same or         different atoms selected from oxygen, sulfur and nitrogen atoms,         which is formed by bonding of R¹ to A¹ or by bonding of R² to         A¹” can be exemplified by cyclobutane ring, cyclopentane ring,         cyclohexane ring, azetidine ring, pyrrolidine ring, pyrroline         ring, piperidine ring, imidazolidine ring, imidazoline ring,         oxazolidine ring, thiazolidine ring, isoxazolidine ring,         isothiazolidine ring, tetra-hydropyridine ring, piperazine ring,         morpholine ring, thiomorpholine ring, dioxazine ring and         dithiazine ring. “The 4- to 7-membered ring which may contain         one or two same or different atoms selected form oxygen, sulfur         and nitrogen atoms, which is formed by bonding of R² to R¹” can         be exemplified by azetidine ring, pyrrolidine ring, pyrroline         ring, piperidine ring, imidazolidine ring, imidazoline ring,         oxazolidine ring, thiazolidine ring, isoxazolidine ring,         isothiazolidine ring, tetrahydropyridine ring, piperazine ring,         morpholine ring, thiomorpholine ring, dioxazine ring and         dithiazine ring.

“Heterocyclic ring” can be exemplified by pyridyl group, pyridine-N-oxide group, pyrimidyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group and pyrazolyl group. “Condensed ring” can be exemplified by naphthalene, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, indole, indoline, coumarone, isocoumarone, benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzothiophene, benzoxazole, benzothiazole, benzimidazole and indazole.

“Salt” can be exemplified by inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate and the like; organic acid salts such as acetate, fumarate, maleate, oxalate, methanesultonate, benzenesulfonate, paratoluenesulfonate and the like; and salts with metal ions such as sodium ion, potassium ion, calcium ion and the like.

The aromatic diamide derivative represented by the general formula (I) or the salt thereof according to the present invention may contain, in the structural formula, one or more asymmetric carbon atoms or asymmetric centers, and may contain two or more kinds of optical isomers or diastereomers; and the present aromatic diamide derivative or salt thereof includes even these individual optical isomers and mixtures of any proportions of the optical isomers. Also, the aromatic diamide derivative represented by the general formula (I) or the salt thereof according to the present invention may contain, in the structural formula, two kinds of geometrical isomers owing to the carbon-to-carbon double bond or carbon-to-nitrogen double bond; and the present aromatic diamide derivative or salt thereof includes even these individual geometrical isomers and mixtures of any proportions of the geometrical isomers.

In a preferred embodiment of the aromatic diamide derivative represented by the general formula (I) or the salt thereof according to the present invention, A¹ is a (C₁-C₄)alkylene group, a (C₃-C₅)-alkenylene group or a (C₁-C₄)alkynylene group; B is —CO— or —C(═N—OR⁴)—(R⁴ is a hydrogen atom or a (C₁-C₃)alkyl group); R¹ is a (C₁-C₃)alkyl group, a (C₁-C₃)alkoxy group, a mono(C₁-C₃)alkylamino group or a di(C₁-C₃)alkylamino group wherein the two alkyl groups may be the same or different; R² and R³ are each a hydrogen atom; Q¹ and Q² are each a carbon atom; X may be the same or different, and is a halogen atom, a nitro group, a halo(C₁-C₆)alkyl group or a halo(C₁-C₆)alkoxy group; Q³ and Q⁴ are each a carbon atom; Q⁵ is a nitrogen atom or a carbon atom; Y may be the same or different, and is a halogen atom, a (C₁-C₆)alkyl group, a halo(C₁-C₆) alkyl group, a (C₁-C₆) alkoxy group, a halo (C₁-C₆)-alkoxy group or a halo (C₁-C₆) alkoxyhalo (C₁-C₆) alkoxy group; m is an integer of 1 to 3; and Z¹ and Z² are each an oxygen atom.

The aromatic diamide derivative represented by the general formula (I) or the salt thereof according to the present invention can be produced, for example, by the processes shown in the following schemes. The present aromatic diamide derivative or salt thereof can also be produced, for example, by the process disclosed in Japanese Patent Application No. 10-350768. However, the processes for producing the present aromatic diamide derivative or salt thereof are not restricted to these processes.

(wherein R¹, R², A¹, B, Q¹ to Q⁵, Y, m, Z¹ and Z² each have the same definition as given above).

A carboxylic anhydride derivative represented by the general formula (II) is reacted with an amine represented by the general formula (III) in the presence of an inert solvent to obtain an imide derivative represented by the general formula (IV); the imide derivative (IV) is reacted, after being isolated or without being isolated, with an amine represented by the general formula (V); thereby, an aromatic diamide derivative represented by the general formula (I) can be produced.

(1) General Formula (II)→General Formula (IV)

The inert solvent usable in the present reaction can be any solvent as long as it does not impair the progress of the present reaction. It can be exemplified by aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and the like; chlorinated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene and the like; chain or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran and the like; esters such as ethyl acetate and the like; amides such as dimethylformamide, dimethylacetamide and the like; acids such as acetic acid and the like; dimethyl sulfoxide; and 1,3-dimethyl-2-imidazolidinone. These inert solvents can be used singly or in admixture of two or more kinds.

Since the present reaction is an equimolar reaction, the individual reactants can be used by the same mole, but any reactant may be used in excess. The present reaction may be conducted under a dehydrating condition as necessary.

The reaction temperature can be room temperature to the refluxing temperature of the inert solvent used. The reaction time varies depending upon, for example, the size or temperature of reaction, but can appropriately be determined in a range of several minutes to 48 hours.

After the completion of the reaction, the reaction mixture containing an intended product is subjected to an isolation treatment according to an ordinary method and, as necessary, purification is conducted by recrystallization, column chromatography or the like, whereby the intended product can be obtained. The reaction mixture per se may be used in the next reaction without being subjected to the above isolation treatment for obtaining the intended product.

The carboxylic anhydride derivative represented by the general formula (II) can be produced by one of the processes described in J. Org. Chem., 52, 129 (1987); J. Am. Chem. Soc., L, 1865 (1929); ibidem, 6, 1542 (1941); etc. The amine represented by the general formula (III) can be produced by one of the processes described in J. Org. Chem., a, 1 (1964); Angew. Chem. Int. Ed. Engl., 24, 871 (1985); Synthesis, 1984, 667; Nippon Kagaku Kaishi, 1973, 2351; DE-2606982; JP-A-1-90163; etc. The amine represented by the general formula (V) can be produced by one of the processes described in Chem. Pharm. Bull., 30(5), 1921-1924 (1982); Jikken Kagaku Koza 22, Organic Synthesis IV (Amino Acids and Peptides) (1992); etc.

(2) General Formula (IV)→General Formula (I)

The inert solvent usable in the present reaction can be exemplified by those inert solvents usable in the above reaction (1).

Since the present reaction is an equimolar reaction, the individual reactants can be used by the same mole, but the amine represented by the general formula (V) may be used in excess.

The reaction temperature can be room temperature to the refluxing temperature of the inert solvent used. The reaction time varies depending upon, for example, the size or temperature of reaction, but can appropriately be determined in a range of several minutes to 48 hours.

After the completion of the reaction, the reaction mixture containing an intended product is subjected to an isolation treatment according to an ordinary method and, as necessary, purification is conducted by recrystallization, column chromatography or the like, whereby the intended product can be obtained.

(wherein R¹, R², R³, A¹, B, Q¹ to Q⁵, Y and m each have the same definition as given above).

A carboxylic anhydride derivative represented by the general formula (II-1) is reacted with an amine represented by the general formula (V) in the presence of an inert solvent to obtain a carboxamide represented by the general formula (VI-2). This carboxamide (VI-2) is subjected to the following procedure after being isolated or without being isolated. That is, the carboxamide (VI-2), wherein R² is a hydrogen atom, is subjected to a condensation reaction in the presence of a condensation agent to obtain a compound represented by the general formula (VII-2); the compound (VII-2) is reacted, after being isolated or without being isolated, with an amine represented by the general formula (III-1) in the presence of an inert solvent; or, the carboxamide (VI-2), wherein R² is other than hydrogen atom, is condensed with an amine represented by the general formula (III-1) in the presence of a condensation agent; thereby, an aromatic diamide derivative represented by the general formula (I-1) can be produced.

Alternatively, a carboxylic anhydride derivative represented by the general formula (II-1) is reacted with an amine represented by the general formula (III-1) in the presence of an inert solvent to obtain a carboxamide represented by the general formula (VI-1). This carboxamide (VI-1) is subjected to the following procedure after being isolated or without being isolated. That is, the carboxamide (VI-1), wherein R³ is a hydrogen atom, is subjected to a condensation reaction in the presence of a condensation agent to obtain a compound represented by the general formula (VII-1) and this compound (VII-1) is reacted, after being isolated or without being isolated, with an amine represented by the general formula. (V) in the presence of an inert solvent; or, the carboxamide (VI-1), wherein R³ is other than hydrogen atom, is condensed with an amine represented by the general formula (V) in the presence of a condensation agent; thereby, an aromatic diamide derivative represented by the general formula (I-1) can be produced.

(1) General Formula (II-1)→General Formula (VI-1), or General Formula (II-1)→General Formula (VI-2)

The present reaction is conducted in the same manner as in the production process 1 (2), whereby an intended compound can be produced.

(2) General Formula (VII-1) or General Formula (VII-2) →General Formula (I-1)

The present reaction is conducted in the same manner as in the production process 1 (2), whereby an intended product can be produced.

(3) General Formula (VI-1)→General Formula (VII-1), or general formula (VI-2)→General Formula (VII-2)

The present reaction is conducted in the same manner as described in J. Med. Chem., 10, 982 (1967), whereby an intended compound can be produced.

(4) General formula (VI-1) or General Formula (VI-2)→General Formula (I-1)

A carboxamide derivative represented by the general formula (VI-1) or the general formula (VI-2) is reacted with an amine represented by the general formula (V) or the general formula (III-1) in the presence of a condensation agent and an inert solvent, whereby an intended compound can be produced. The present invention may be conducted in the presence of a base, as necessary.

The inert solvent used in the present reaction can be exemplified by tetrahydrofuran, diethyl ether, dioxane, methylene chloride and chloroform.

The condensation agent used in the present reaction can be any condensation agent used in ordinary amide production, and can be exemplified by Mukaiyama reagent (2-choro-N-methylpyridinium iodide), DCC (1,3-dicyclohexylcarbodiimide), CDI (carbonyl diimidazole) and DEPC (diethyl phosphoric cyanide). The amount of the condensation agent used can appropriately be determined at one or more moles per mole of the carboxamide represented by the general formula (VI-1) or the general formula (VI-2)

The base usable in the present reaction can be exemplified by organic bases (e.g. triethylamine and pyridine) and inorganic bases (e.g. potassium carbonate). The amount of the base used can appropriately be determined at one or more moles per mole of the carboxamide represented by the general formula (VI-1) or the general formula (VI-2).

The reaction temperature can be 0° C. to the boiling point of the inert solvent used. The reaction time varies depending upon, for example, the size or temperature of reaction, but is several minutes to 48 hours.

After the completion of the reaction, the reaction mixture containing an intended product is subjected to an isolation treatment according to an ordinary method and, as necessary, purification is conducted by recrystallization, column chromatography or the like, whereby the intended product can be obtained.

Representative compounds of the aromatic diamide derivative represented by the general formula (I) are shown below in Table 1, Table 2 and Table 3. However, the present aromatic diamide derivative is not restricted to these compounds. In the following tables, Me refers to methyl group; Et refers to ethyl group; Pr refers to propyl group; Bu refers to butyl group; Ph refers to phenyl group; Pyr refers to pyridyl group; c− refers to alicyclic hydrocarbon group; and Physical property refers to melting point (° C.).

In Table 1, with respect to Q¹ to Q⁴ which are each C—X, Q¹ is at 3-position; Q² is at 4-position; Q³ is at 5-position; and Q⁴ is at 6-position.

TABLE 1 General formula (I)

(Q¹ = Q² = Q³ = Q⁴ = C—X, Q⁵ = C, Z¹ = Z² = O, R³ = H) Physical No. —A¹—B—R¹ R² X Ym property 1 CH₂CO₂Et H 3-F 2-Me-4-CF(CF₃)₂ 120 2 CH₂CO₂Et H 3-Cl 2-Me-4-CF(CF₃)₂ 103 3 CH₂CO₂Et H 3-Br 2-Me-4-CF(CF₃)₂ 134 4 CH₂CO₂Et H 3-I 2-Me-4-CF(CF₃)₂ 120 5 CH(Me)CO₂Et H 3-F 2-Me-4-CF(CF₃)₂ 140 6 CH(Me)CO₂Et H 3-I 2-Me-4-CF(CF₃)₂ 145 7 CH(Me)CH₂CO₂Et H 3-F 2-Me-4-CF(CF₃)₂  88 8 CH₂CH₂CO₂Et H 3-I 2-Me-4-CF₂CF₃ 112 9 CH₂CH₂CO₂Et H 3-I 2-Me-4-CF(CF₃)₂ 133 10 CH₂CH₂CO₂Et H 6-I 2-Me-4-CF(CF₃)₂ 164 11 CH(Me)CH₂CO₂Et H 3-I 2-Me-4-CF(CF₃)₂ paste 12 CH(Me)CH₂CO₂Me H 3-I 2-Me-4-CF(CF₃)₂ 13 CH(Me)CH₂CO₂Pr-i H 3-I 2-Me-4-CF(CF₃)₂ 14 CH(Me)CH₂CO₂Bu-t H 3-I 2-Me-4-CF(CF₃)₂ 15 CH(Me)CH₂CO₂Et H 4-I 2-Me-4-CF(CF₃)₂ 16 CH(Me)CH₂CO₂Et H 3-CF₃ 2-Me-4-CF₂CF₃ 17 CH(Me)CH₂CO₂Et H 3-OCF₃ 2-Cl-4-CF(CF₃)₂ 18 CH(Me)CH₂CO₂Et H 3-I 2-Et-4-CF(CF₃)₂ 19 CH(Me)CH₂CO₂Et H 3-I 2-Me-4-CH═C(Cl)CF₃ 20 CH(Me)CH₂CO₂Et H 3-I 2-Me-4-CH═CBr₂ 21 CH(Me)CH₂CO₂Et H 3-I 4-CO₂CH(CF₃)₂ 22 CH(Me)CH₂CO₂Et H 3-I 2-Me-4-C≡C- (2,4-Cl₂—Ph) 23 CH(Me)CH₂CO₂Et H 3-I 2-Me-4-C≡C—Bu-t 24 CH(Me)CH₂CO₂Et H 3-CF₃ 2-F-4-CF₂CF₃ 25 CH(Me)CH₂CO₂Et H 3-I 2-OMe-4-CF(CF₃)₂ 26 CH(Me)CH₂CO₂Et H 3-I 2-Me-4-C(CH₃)═NOMe 27 CH(Me)CH₂CO₂Et H 3-I 2-Me-4-C(CH₃)═NO— CH₂—Ph 28 CH(Me)CH₂CO₂Et H 3-I 3-OCF₂CF₂O-4 29 CH(Me)CH₂CO₂Et H 3-I 3-OCF₂CF₂-4 30 CH(Me)CH₂CO₂Et H 3-I 2-Cl-3-OCF₂CF₂O-4 31 CH(Me)CH₂CO₂Et H 3-I 3-OCF₂O-4 32 CH(Me)CH₂CO₂Et H 3-I 3-OCHFCF₂O-4 33 CH(Me)CH₂CO₂Et H 3-I 3-OCF₃CHFO-4 34 CH(Me)CH₂CO₂Et H 3-I 2-Me-3-F-4-CF(CF₃)₂ 35 CH(Me)CH₂CO₂Et H 3-I 2-Me-5-F-4-CF(CF₃)₂ 36 CH(Me)CH₂CO₂Et H 3-I 2-Me-4-(4-CF₃—Ph) 37 CH(Me)CH₂CO₂Et H 3-I 2-Me-4-(4-Cl—Ph) 38 CH(Me)CH₂CO₂Et H 3-I 2-Me-4-(4-Cl—PhO) 39 CH(Me)CO₂Et H 3-I 2-Me-4-OCF₃ 40 CH(Me)CO₂Et H 3-I 2-Me-4-OCF₂CF₃ 41 CH(Me)CO₂Et H 3-I 2-Me-4-CF₃ 42 CH(Me)CO₂Et H 3-I 2-Me-3-CF₂CF₃ 43 CH(Me)CO₂Et H 3-I 2-Me-4-SCF₃ 44 CH(Me)CO₂Et H 3-I 2-Me-4-SOCF₃ 45 CH(Me)CO₂Et H 3-I 2-Me-4-SO₂CF₃ 46 CH(Me)CH₂CO₂Et H 3-I 2-Me-4-SCF₂CF₃ 47 CH(Me)CO₂Et H 3-I 2-Me-4-OCF₂CHFOCF₃ 48 CH(Me)CO₂Et H 3-I 2-Me-4-(5-CF₃-2- Pyr—O) 49 CH(Me)CO₂Et H 3-Cl 2-Me-4-(3-Cl-5- CF₃-2-Pyr—O) 50 CH(Me)CH₂CO₂Et H 3-NO₂ 2-Me-4-CF(CF₃)₂ 51 CH(Me)CH₂CO₂Et H 3,4-Cl₂ 2-Me-4-CF(CF₃)₂ 52 CH(Me)CH₂CO₂Et H 3-SCF₃ 2-Me-4-CF(CF₃)₂ 53 CH(Me)CH₂CO₂Et H 3-SOCF₃ 2-Me-4-CF(CF₃)₂ 54 CH(Me)CH₂CO₂Et H 3-SO₂CF₃ 2-Me-4-CF(CF₃)₂ 55 CH(Me)CH₂CO₂Et H 3-Ph 2-Me-4-CF(CF₃)₂ 56 CH(Me)CH₂CO₂Et H 3-OPh 2-Me-4-CF(CF₃)₂ 57 CH(Me)CH₂CO₂Et H 3-(4- 2-Me-4-CF(CF₃)₂ Cl—Pho) 58 CH(Me)CO₂Et H 3-I 2-Me-4-Cl 59 CH(Me)CO₂Et H 3- 2-Me-4-Cl CONHPr-i 60 CH(Me)CH₂CO₂Et H 3-CH═CH— 2-Me-4-Cl CH═CH-4 61 CH(Me)CH₂CO₂Et Me 3-I 2-Me-4-CF(CF₃)₂ 62 CH(Me)CH₂CO₂Et Et 3-I 2-Me-4-CF(CF₃)₂ 63 C(Me)₂C≡CCO₂Et H 3-I 2-Me-4-CF(CF₃)₂ 64 C(Me)₂CH═CHCO₂Et H 3-I 2-Me-4-CF(CF₃)₂ 250 65 CH(CH₂SMe)CH₂CO₂Et H 3-I 2-Me-4-CF(CF₃)₂ 66 CH(CF₃)CH₂CO₂Et H 3-I 2-Me-4-CF(CF₃)₂ 67 CH(CH₂OMe)CH₂CO₂Et H 3-I 2-Me-4-CF(CF₃)₂ 68 CH(Ph)CH₂CO₂Et H 3-I 2-Me-4-CF(CF₃)₂ 69 CH(4-Cl—Ph)CH₂CO₂Et H 3-I 2-Me-4-CF(CF₃)₂ 70 CH(Me)CON(Me)₂ H 3-I 2-Me-4-CF₂CF₃ 122 71 CH(Me)CON(Me)₂ H 3-I 2-Me-4-CF(CF₃)₂ 156 72 CH(Me)CON(Et)₂ H 3-I 2-Me-4-CF(CF₃)₂ 133 73 CH(Me)CH₂CONHMe H 3-I 2-Me-4-CF(CF₃)₂ 220 74 CH(Me)CH₂CONHEt H 3-I 2-Me-4-CF(CF₃)₂ 208 75 CH(Me)CH₂CON(Me)Ph H 3-I 2-Me-4-CF(CF₃)₂ 200 76 CH(Me)CH₂CON(Me)₂ H 3-I 2-Me-4-CF₂CF₃ 102 77 CH(Me)CH₂CON(Me)₂ H 3-I 2-Me-4-CF(CF₃)₂ 126 78 CH(Me)CH₂CON(Et)₂ H 3-I 2-Me-4-CF(CF₃)₂ 137 79 CH(Me)CH₂CONHEt H 4-I 2-Me-4-CF(CF₃)₂ 80 CH(Me)CH₂CONHEt H 3-CF₃ 2-Me-4-CF₂CF₃ 81 CH(Me)CH₂CONHEt H 3-OCF₃ 2-Cl-4-CF(CF₃)₂ 82 CH(Me)CH₂CONHEt H 3-I 2-Et-4-CF(CF₃)₂ 83 CH(Me)CH₂CONHEt H 3-I 2-Me-4-CH═ C(Cl)CF₃ 84 CH(Me)CH₂CONHEt H 3-I 2-Me-4-CH═CBr₂ 85 CH(Me)CON(Et)₂ H 3-I 4-CO₂CH(CF₃)₂ 86 CH(Me)CON(Et)₂ H 3-I 2-Me-4-C≡C- (2,4-Cl₂—Ph) 87 CH(Me)CH₂CONHEt H 3-I 2-Me-4-C≡C—Bu-t 88 CH(Me)CH₂CON(Et)₂ H 3-CF₃ 2-F-4-CF₂CF₃ 89 CH(Me)CH₂CON(Et)₂ H 3-I 2-OMe-4-CF(CF₃)₂ 90 CH(Me)CH₂CON(Et)₂ H 3-I 2-Me-4-C(CH₃)═ NOMe 91 CH(Me)CH₂CON(Et)₂ H 3-I 2-Me-4-C(CH₃)═ NO—CH₂—Ph 92 CH(Me)CH₂CON(Et)₂ H 3-I 3-OCF₂CF₂O-4 93 CH(Me)CH₂CONHEt H 3-I 3-OCF₂CF₂-4 94 CH(Me)CON(Et)₂ H 3-I 2-Cl-3-OCF₂CF₂O-4 95 CH(Me)CH₂CON(Et)₂ H 3-I 3-OCF₂O-4 96 CH(Me)CH₂CONHEt H 3-I 3-OCHFCF₂O-4 97 CH(Me)CON(Et)₂ H 3-I 3-OCF₂CHFO-4 98 CH(Me)CH₂CON(Et)₂ H 3-I 2-Me-3-F- 4-CF(CF₃)₂ 99 CH(Me)CH₂CONHEt H 3-I 2-Me-5-F-4-CF(CF₃)₂ 100 CH(Me)CON(Et)₂ H 3-I 2-Me-4-(4-CF₃—Ph) 101 CH(Me)CH₂CON(Et)₂ H 3-I 2-Me-4-(4-Cl—Ph) 102 CH(Me)CH₂CONHEt H 3-I 2-Me-4-(4-Cl—PhO) 103 CH(Me)CON(Et)₂ H 3-I 2-Me-4-OCF₃ 104 CH(Me)CH₂CON(Et)₂ H 3-I 2-Me-4-OCF₂CF₃ 105 CH(Me)CH₂CONHEt H 3-I 2-Me-4-CF₃ 106 CH(Me)CH₂CONHEt H 3-I 2-Me-3-CF₂CF₃ 107 CH(Me)CON(Et)₂ H 3-I 2-Me-4-SCF₃ 108 CH(Me)CH₂CON(Et)₂ H 3-I 2-Me-4-SOCF₃ 109 CH(Me)CH₂CONHEt H 3-I 2-Me-4-SO₂CF₃ 110 CH(Me)CH₂CONHEt H 3-I 2-Me-4-SCF₂CF₃ 111 CH(Me)CON(Et)₂ H 3-I 2-Me-4-OCF₂CHFOCF₃ 112 CH(Me)CH₂CON(Et)₂ H 3-I 2-Me-4-(5-CF₃-2- Pyr—O) 113 CH(Me)CH₂CONHEt H 3-Cl 2-Me-4-(3-Cl-5- CF₃-2-Pyr—O) 114 CH(Me)CH₂CONHEt H 3-NO₂ 2-Me-4-CF(CF₃)₂ 115 CH(Me)CON(Et)₂ H 3,4-Cl₂ 2-Me-4-CF(CF₃)₂ 116 CH(Me)CH₂CON(Et)₂ H 3-SCF₃ 2-Me-4-CF(CF₃)₂ 117 CH(Me)CH₂CONHEt H 3-SOCF₃ 2-Me-4-CF(CF₃)₂ 118 CH(Me)CH₂CONHEt H 3-SO₂CF₃ 2-Me-4-CF(CF₃)₂ 119 CH(Me)CON(Et)₂ H 3-Ph 2-Me-4-CF(CF₃)₂ 120 CH(Me)CH₂CON(Et)₂ H 3-OPh 2-Me-4-CF(CF₃)₂ 121 CH(Me)CH₂CONHEt H 3-(4- 2-Me-4-CF(CF₃)₂ Cl—PhO) 122 CH(Me)CON(Et)₂ H 3-I 2-Me-4-Cl 123 CH(Me)CH₂CON(Et)₂ H 3- 2-Me-4-Cl CONHPr-i 124 CH(Me)CH₂CONHEt H 3-CH═CH— 2-Me-4-Cl CH═CH-4 125 CH(Me)CON(Et)₂ Me 3-I 2-Me-4-CF(CF₃)₂ 126 CH(Me)CH₂CON(Et)₂ Et 3-I 2-Me-4-CF(CF₃)₂ 127 C(Me)₂C≡CCON(Et)₂ H 3-I 2-Me-4-CF(CF₃)₂ 128 C(Me)₂CH═ H 3-I 2-Me-4-CF(CF₃)₂ CHCON(Et)₂ 129 CH(CH₂SMe)CH₂CON— H 3-I 2-Me-4-CF(CF₃)₂ (Et)₂ 130 CH(CF₃)CH₂CONHEt H 3-I 2-Me-4-CF(CF₃)₂ 131 CH(CH₂OMe)— H 3-I 2-Me-4-CF(CF₃)₂ CH₂CONHEt 132 CH(Ph)CH₂CON(Et)₂ H 3-I 2-Me-4-CF(CF₃)₂ 133 CH(4-Cl—Ph)— H 3-I 2-Me-4-CF(CF₃)₂ CH₂CONHEt 134 CH(Me)COMe H 3-I 2-Me-4-CF(CF₃)₂ 189 135 CH(Me)COPh H 3-I 2-Me-4-CF(CF₃)₂ 171 136 CH(Me)CH═NOMe H 3-I 2-Me-4-CF(CF₃)₂ 192 137 CH(Me)CH═NOMe H 6-I 2-Me-4-CF(CF₃)₂ paste 138 CH(Me)CH═NOCH₂Ph H 3-I 2-Me-4-CF(CF₃)₂ paste 139 C(Me)₂CH═NOMe H 3-I 2-Me-4-CF(CF₃)₂ 126 140 CH(Me)C(Me)═NOMe H 3-I 2-Me-4-CF(CF₃)₂ 107 141 CH₂C(Ph)═NOMe H 3-I 2-Me-4-CF(CF₃)₂ 106 142 CH(Me)CH═NOMe H 4-I 2-Me-4-CF(CF₃)₂ 143 CH(Me)C(Me)═NOMe H 3-CF₃ 2-Me-4-CF₂CF₃ 144 CH(Me)CH═NOMe H 3-OCF₃ 2-Cl-4-CF(CF₃)₂ 145 C(Me)₂CH═NOMe H 3-I 2-Et-4-CF(CF₃)₂ 146 CH(Me)CH═NOMe H 3-I 2-Me-4-CH═C(Cl)CF₃ 147 CH(Me)C(Me)═NOMe H 3-I 2-Me-4-CH═CBr₂ 148 CH(Me)CH═NOMe H 3-I 4-CO₂CH(CF₃)₂ 149 C(Me)₂CH═NOMe H 3-I 2-Me-4-C≡C- (2,4-Cl₂—Ph) 150 CH(Me)CH═NOMe H 3-I 2-Me-4-C≡C—Bu-t 151 CH₂C(Me)═NOMe H 3-CF₃ 2-F-4-CF₂CF₃ 152 CH(Me)CH═NOMe H 3-I 2-OMe-4-CF(CF₃)₂ 153 C(Me)₂CH═NOMe H 3-I 2-Me-4-C(CH₃)═NOMe 154 CH(Me)CH═NOMe H 3-I 2-Me-4-C(CH₃)═NO— CH₂—Ph 155 CH(Me)C(Me)═NOMe H 3-I 3-OCF₂CF₂O-4 156 CH(Me)CH═NOMe H 3-I 3-OCF₂CF₂-4 157 C(Me)₂CH═NOMe H 3-I 2-Cl-3-OCF₂CF₂O-4 158 CH(Me)C(Me)═NOMe H 3-I 3-OCF₂O-4 159 CH(Me)CH═NOMe H 3-I 3-OCHFCF₂O-4 160 C(Me)₂CH═NOMe H 3-I 3-OCF₂CHFO-4 161 CH(Me)CH═NOMe H 3-I 2-Me-3-F-4-CF(CF₃)₂ 162 CH(Me)C(Me)═NOMe H 3-I 2-Me-5-F-4-CF(CF₃)₂ 163 CH(Me)CH═NOMe H 3-I 2-Me-4-(4-CF₃—Ph) 164 C(Me)₂CH═NOMe H 3-I 2-Me-4-(4-Cl—Ph) 165 CH(Me)CH═NOMe H 3-I 2-Me-4-(4-Cl—PhO) 166 CH(Me)C(Me)═NOMe H 3-I 2-Me-4-OCF₃ 167 CH(Me)CH═NOMe H 3-I 2-Me-4-OCF₂CF₃ 168 C(Me)₂CH═NOMe H 3-I 2-Me-4-CF₃ 169 CH(Me)CH═NOMe H 3-I 2-Me-3-CF₂CF₃ 170 CH(Me)C(Me)═NOMe H 3-I 2-Me-4-SCF₃ 171 CH(Me)CH═NOMe H 3-I 2-Me-4-SOCF₃ 172 C(Me)₂CH═NOMe H 3-I 2-Me-4-SO₂CF₃ 173 CH(Me)CH═NOMe H 3-I 2-Me-4-SCF₂CF₃ 174 CH(Me)CH═NOMe H 3-I 2-Me-4-OCF₂CHFOCF₃ 175 C(Me)₂CH═NOMe H 3-I 2-Me-4-(5-CF₃-2- Pyr—O) 176 CH(Me)CH═NOMe H 3-Cl 2-Me-4-(3-Cl-5- CF₃-2-Pyr—O) 177 C(Me)₂CH═NOMe H 3-NO₂ 2-Me-4-CF(CF₃)₂ 149 178 CH(Me)CH═NOMe H 3,4-Cl₂ 2-Me-4-CF(CF₃)₂ 179 CH(Me)CH═NOMe H 3-SCF₃ 2-Me-4-CF(CF₃)₂ 180 C(Me)₂CH═NOMe H 3-SOCF₃ 2-Me-4-CF(CF₃)₂ 181 CH(Me)CH═NOMe H 3-SO₂CF₃ 2-Me-4-CF(CF₃)₂ 182 C(Me)₂CH═NOMe H 3-Ph 2-Me-4-CF(CF₃)₂ 183 CH(Me)CH═NOMe H 3-OPh 2-Me-4-CF(CF₃)₂ 184 CH(Me)CH═NOMe H 3-(4-Cl— 2-Me-4-CF(CF₃)₂ PhO) 185 C(Me)₂CH═NOMe H 3-I 2-Me-4-Cl 186 CH(Me)CH═NOMe H 3- 2-Me-4-Cl CONHPr-i 187 CH(Me)CH═NOMe H 3-CH═CH— 2-Me-4-Cl CH═CH-4 188 CH(Me)CH═NOMe Me 3-I 2-Me-4-CF(CF₃)₂ 189 CH(Me)CH═NOMe Et 3-I 2-Me-4-CF(CF₃)₂ 190 CH(CH₂SMe)CH═NOMe H 3-I 2-Me-4-CF(CF₃)₂ 191 CH(CF₃)CH═NOEt H 3-I 2-Me-4-CF(CF₃)₂ 192 CH(CH₂OMe)CH═NOMe H 3-I 2-Me-4-CF(CF₃)₂ 193 CH(Ph)CH═NOMe H 3-I 2-Me-4-CF(CF₃)₂ 194 CH(Me)CH₂CH═NOMe H 3-I 2-Me-4-CF(CF₃)₂ 195 CH(Me)CH═NOCH₂- H 3-I 2-Me-4-CF(CF₃)₂ (4-t-Bu—Ph) 196 CH(Me)CH═NOCH₂- H 3-I 2-Me-4-CF(CF₃)₂ (4-t-BuO₂C—Ph) 197 CH(Me)CO₂CH₂CH₂OEt H 3-I 2-Me-4-CF(CF₃)₂ 198 CH(Me)CO₂CH₂CH₂SEt H 3-I 2-Me-4-CF(CF₃)₂ 199 CH(Me)CO₂CH₂—Ph H 3-I 2-Me-4-CF(CF₃)₂ 200 CH₂CH═CHCO₂Et H 3-I 2-Me-4-CF(CF₃)₂ 201 CH₂C≡CCO₂Et H 3-I 2-Me-4-CF(CF₃)₂ 202 CH(Me)CH═CHCO₂Et H 3-I 2-Me-4-CF(CF₃)₂ 203 CH(Me)C≡CCO₂Et H 3-I 2-Me-4-CF(CF₃)₂ 204 CH(Me)CONHEt H 3-I 2-Me-4-CF(CF₃)₂ 210 205 CH(Me)CONHPr-n H 3-I 2-Me-4-CF(CF₃)₂ 201 206 CH(Me)CONHPr-c H 3-I 2-Me-4-CF(CF₃)₂ 207 CH(Me)CONHBu-n H 3-I 2-Me-4-CF(CF₃)₂ 214 208 CH(Me)CONHCH₂CH═CH₂ H 3-I 2-Me-4-CF(CF₃)₂ 209 CH(Me)CONHCH₂C≡CH H 3-I 2-Me-4-CF(CF₃)₂ 210 CH(Me)CONHCH₂CF₃ H 3-I 2-Me-4-CF(CF₃)₂ 211 CH(Me)CONHCH₂CH₂SMe H 3-I 2-Me-4-CF(CF₃)₂ 212 CH(Me)CONHCH₂CH₂SOMe H 3-I 2-Me-4-CF(CF₃)₂ 213 CH(Me)CONHCH₂CH₂— H 3-I 2-Me-4-CF(CF₃)₂ SO₂Me 214 CH(Me)CONHCH₂CH₂OMe H 3-I 2-Me-4-CF(CF₃)₂ 215 CH(Me)CONHCH₂—Ph H 3-I 2-Me-4-CF(CF₃)₂ 212 216 CH(Me)CON(n-Pr)₂ H 3-I 2-Me-4-CF(CF₃)₂ 142 217 CH(Me)CON(CH₂CH₂)₂O H 3-I 2-Me-4-CF(CF₃)₂ 165 218 CH(Me)CON(CH₂)₅ H 3-I 2-Me-4-CF(CF₃)₂ 170 219 CH(Me)CON(CH₂)₄ H 3-I 2-Me-4-CF(CF₃)₂ 205 220 C(Me)₂CONHEt H 3-I 2-Me-4-CF(CF₃)₂ 221 C(Me)₂CONHPr-n H 3-I 2-Me-4-CF(CF₃)₂ 222 CH(Me)CONHCH₂CH═CH₂ H 3-I 2-Me-4-CF(CF₃)₂ 223 CH(Me)CONHCH₂C≡CH H 3-I 2-Me-4-CF(CF₃)₂ 224 CH(Me)CH═CHCONHMe H 3-I 2-Me-4-CF(CF₃)₂ 225 CH(Me)C≡CCONHEt H 3-I 2-Me-4-CF(CF₃)₂ 226 C(Me)₂CH═CHCONHEt H 3-I 2-Me-4-CF(CF₃)₂ 245 227 C(Me)₂C≡CCONHEt H 3-I 2-Me-4-CF(CF₃)₂ 228 CH(Me)C(═O)H H H 2-Me-4-OCF₃ 134 229 C(Me)₂C(═O)H H H 2-Me-4-OCF₃ 150 230 C(Me)₂C(═O)H H H 2-Me-4- 159 OCF₂CHFOC₃F₇-n 231 C(Me)₂C(═O)H H H 2-Me-4-OCF₂CHFCF₃ 171 232 C(Me)₂C(═O)H H H 2-Me-4-O-(3-Cl- 159 5-CF₃-2-Pyr) 233 C(Me)₂C(═O)H H H 2-Me-4-Cl 229 234 C(Me)₂C(═O)H H H 2-Me-4-CF₂CF₃  87 235 C(Me)₂C(═O)H H H 2-Me-4-CF₂CF₂CF₃ 143 236 C(Me)₂C(═O)H H H 2-Me-4-CF(CF₃)₂ 214 237 C(Me)₂C(═O)H H 3-NO₂ 2-Me-4-CF(CF₃)₂ 262 238 C(Me)₂C(═O)H H 3-F 2-Me-4-CF(CF₃)₂ 146 239 C(Me)₂C(═O)H H 3,4- 2-Me-4-CF(CF₃)₂ 166 Cl₂ 240 (CH₂)₂C(═O)H H 3-I 2-Me-4-CF(CF₃)₂ 128 241 CH(CH₂SO₂Me)C(═O)H H 3-I 2-Me-4-CF(CF₃)₂ 106 242 C(Me)(CH₂SO₂Me)— H 3-I 2-Me-4-CF(CF₃)₂ 118 C(═O)H 243 C(Me)(CH₂SO₂Et)— H 3-I 2-Me-4-CF(CF₃)₂ 103 C(═O)H 244 C(Me)₂CH═NOH H H 2-Me-4-OCF₂CHFCF₃ 150 245 C(Me)₂CH═NOH H H 2-Me-4-CF₂CF₃ 182 246 C(Me)₂CH═NOH H 3-I 2-Me-4-CF₂CF₃ 189 247 C(Me)₂CH═NOH H 3-F 2-Me-4-CF(CF₃)₂ 242 248 C(Me)₂CH═NOH H 3-I 2-Me-4-CF(CF₃)₂ 218 249 C(Me)(CH₂SO₂Me)CH═ H 3-I 2-Me-4-CF(CF₃)₂ 106 NOH 250 C(Me)(CH₂SO₂Et)CH═ H 3-I 2-Me-4-CF(CF₃)₂ 112 NOH 251 CH₂CH═NOMe Me H 2-Me-4-CF(CF₃)₂ 127 252 CH(Me)CH═NOMe H H 2-Me-4-OCF₃ 133 253 CH(Me)CH═NOMe H 3-I 2-Me-4-OCF₃ 159 254 CH(Me)CH═NOMe H 3-Br 2-Me-4-OCF₃ 168 255 CH(Me)CH═NOMe H H 2-Me-4-CF₂CF₃ 130 256 CH(Me)CH═NOMe H 3-I 2-Me-4-CF₂CF₃ 110 257 CH(Me)CH═NOMe H 3-Cl 2-Me-4-CF₂CF₃ 154 258 CH(Me)CH═NOMe H 3-Br 2-Me-4-CF₂CF₃ 162 259 CH(Me)CH═NOMe H H 2-Me-4-CF(CF₃)₂ 154 260 CH(Me)CH═NOMe H 3-OCF₃ 2-Me-4-CF(CF₃)₂ 165 261 C(Me)₂CH═NOMe H H 2-Me-4-OCHF₂ 170 262 C(Me)₂CH═NOMe H 3-I 2-Me-4-OCHF₂ 184 (E-form) 263 C(Me)₂CH═NOMe H 3-I 2-Me-4-OCHF₂ 182 (Z-form) 264 C(Me)₂CH═NOMe H H 2-Me-4-OCF₃ 195 265 C(Me)₂CH═NOMe H 3-I 2-Me-4-OCF₃ 191 266 C(Me)₂CH═NOMe H 3-Cl 2-Me-4-OCF₃ 199 267 C(Me)₂CH═NOMe H 3-Br 2-Me-4-OCF₃ 184 268 C(Me)₂CH═NOMe H 3,4- 2-Me-4-OCF₃ 212 Cl₂ 269 C(Me)₂CH═NOMe H H 2-Me-4-OCF₂CHF₂ 174 270 C(Me)₂CH═NOMe H 3-I 2-Me-4-OCF₂CHF₂ 185 271 C(Me)₂CH═NOMe H H 2-Me-4-OCF₂CHFCF₃ 160 272 C(Me)₂CH═NOMe H H 2-Me-4- 140 OCF₂CHFOC₃F₇-n 273 C(Me)₂CH═NOMe H H 2-Me-4-O-(3-Cl-5- 151 CF₃-2-Pyr) 274 C(Me)₂CH═NOMe H H 2-Me-4-Cl 178 275 C(Me)₂CH═NOMe H H 2-Me-4-CF₂CF₃ 200 276 C(Me)₂CH═NOMe H 3-I-4- 2-Me-4-CF₂CF₃ 225 Cl 277 C(Me)₂CH═NOMe H 3-I 2-Me-4-CF₂CF₃ 147 278 C(Me)₂CH═NOMe H 3-Cl 2-Me-4-CF₂CF₃ 202 279 C(Me)₂CH═NOMe H 3-Br 2-Me-4-CF₂CF₃ 207 280 C(Me)₂CH═NOMe H H 2-Me-4-CF₂CF₂CF₃ 174 281 C(Me)₂CH═NOMe H H 2-Me-4-CF(CF₃)₂ 178 282 C(Me)₂CH═NOMe H 4-CF₃ 2-Me-4-CF(CF₃)₂ 155 283 C(Me)₂CH═NOMe H 3-OCF₃ 2-Me-4-CF(CF₃)₂ 186 284 C(Me)₂CH═NOMe H 3-F 2-Me-4-CF(CF₃)₂ 199 285 C(Me)₂CH═NOMe H 3-Cl 2-Me-4-CF(CF₃)₂ 234 286 C(Me)₂CH═NOMe H 3-Br 2-Me-4-CF(CF₃)₂ 243 287 C(Me)₂CH═NOMe H 3,4- 2-Me-4-CF(CF₃)₂ 207 Cl₂ 288 C(Me)₂CH═NOMe H H 2-Cl-4-CF₃ 154 289 C(Me)₂CH═NOMe H 3-I 2-Cl-4-CF₃ 167 290 C(Me)₂CH═NOEt H H 2-Me-4-CF(CF₃)₂ 157 291 C(Me)₂CH═NOEt H 3-I 2-Me-4-CF(CF₃)₂ 119 292 CH(Me)CH═NOPr-n H H 2-Me-4-CF(CF₃)₂ 172 293 CH(Me)CH═NOCH₂Pr-c H H 2-Me-4-CF₂CF₃  91 294 CH(Me)CH═NOCH₂CH₂SEt H H 2-Me-4-CF₂CF₃ paste 295 CH(Me)CH═NOCH₂CH₂OEt H H 2-Me-4-CF₂CF₃ paste 296 CH(Me)CH═NOCH₂CH═CH₂ H H 2-Me-4-CF(CF₃)₂ 172 297 C(Me)₂CH═NOCH₂CO₂Et H 3-I 2-Me-4-CF₂CF₃ 298 C(Me)₂CH═ H H 2-Me-4-OCF₃ 153 NOCH₂CO₂Bu-t 299 C(Me)₂CH═NOCH₂CONHEt H H 2-Me-4-CF(CF₃)₂ 300 C(Me)₂CH═NOCH₂CONHEt H 3-I 2-Me-4-CF(CF₃)₂ 301 C(Me)₂CH═ H H 2-Me-4-CF(CF₃)₂ NOCH₂CON(Et)₂ 302 C(Me)₂CH═ H H 2-Me-4-OCF₃ 131 NOCH₂CON(Et)₂ 303 C(Me)₂CH═ H 3-I 2-Me-4-CF(CF₃)₂ NOCH₂CON(Et)₂ 304 (CH₂)₂CH═NOMe H 3-I 2-Me-4-CF(CF₃)₂ 197 305 (CH₂)₃CH═NOMe H H 2-Me-4-OCF₃ 108 306 (CH₂)₃CH═NOEt H H 2-Me-4-OCF₃ 107 307 (CH₂)₄CH═NOMe H H 2-Me-4-OCF₃ 110 308 (CH₂)₄CH═NOEt H H 2-Me-4-OCF₃ 117 309 CH(Me)CH₂CH═NOMe H 3-I 2-Me-4-CF(CF₃)₂ 170 310 C(Me)₂CH═NOMe H 3-I 2-Me-4-OCF₂CHFCF₃ 188 311 C(Me)₂CH═NOMe H H 2-Me-4-O-(3-Cl-5- 170 CF₃-2-Pyr) 312 C(Me)₂CH═NOMe H H 3-OCF₂O-4 181 313 C(Me)₂CH═NOMe H H 3-OCF₂CF₂O-4 191 314 CH(Me)CH═NOCH₂Pr-c H 3-I 2-Me-4-CF(CF₃)₂ 142 315 CH(Me)CH═NOCH₂CH₂SEt H 3-I 2-Me-4-CF(CF₃)₂ 165 316 CH(Me)CH═NOCH₂CH₂OEt H 3-I 2-Me-4-CF(CF₃)₂ 107 317 CH(Me)CH═NOCH₂CH═CHOEt H 3-I 2-Me-4-CF(CF₃)₂ 103 318 C(Me)₂CH═NOCH₂COOBu-t H 3-I 2-Me-4-CF(CF₃)₂ 101 319 C(Me)₂CH═NOCH₂CONEt₂ H 3-I 2-Me-4-CF(CF₃)₂  97 320 CH(Me)CONHCH₂CH₂OMe H 3-I 2-Me-4-CF(CF₃)₂ 200 321 CH(Me)CONHCH₂CH₂— H 3-I 2-Me-4-CF(CF₃)₂ 203 CH₂SMe 322 CH(Me)CONHCH₂CF₃ H 3-I 2-Me-4-CF(CF₃)₂ 236

TABLE 2 (Q¹═Q²═Q³═Q⁴═Q⁵═C, Z¹═S, Z²═O, R³═ H) Physical No. —A¹—B—R¹ R² X Ym property II-1 CH(Me)CH═NOMe H 3-Cl 2-Me-4-CF(CF₃)₂ II-2 CH(Me)C(Me)═NOMe H H 2-Me-4-CF(CF₃)₂ II-3 CH(Me)CH₂CO₂Et H 3-Cl 2-Me-4-CF(CF₃)₂ II-4 CH(Me)CON(Et)₂ H 3-Cl 2-Me-4-CF(CF₃)₂ II-5 CH(Me)CH₂CONHEt H 3-Cl 2-Me-4-CF(CF₃)₂

TABLE 3 (R²═R³═H, Z^(═Z) ^(2═O)) Physical No. —A¹—B—R¹ Q¹ Q² Q³ Q⁴ Q⁵ Ym Property III-1 CH(Me)CONHMe C-I CH CH CH N 2-Me-6-OCF(CF₃)₂ III-2 CH(Me)CON(Me)₂ C-I CH CH CH N 2-Me-6-OCF(CF₃)₂ III-3 C(Me)₂CH═NOH C-I CH CH CH N 2-Me-6-OCF(CF₃)₂ 192 III-4 C(Me)₂CH═NOMe CH CH CH CH N 2-Me-6-OCF(CF₃)₂ III-5 C(Me)₂CH═NOMe C-I CH CH CH N 2-Me-6-OCF(CF₃)₂ 198 III-6 CH(Me)CONHEt CH CH CH CH N 2-Me-6-OCF(CF₃)₂ 220 III-7 CH(Me)CON(Et)₂ CH CH CH CH N 2-Me-6-OCF(CF₃)₂ III-8 CH(Me)C(═O)H CH CH CH CH N 2-Me-6-OCF(CF₃)₂ III-9 CH(Me)CH═NOH CH CH CH CH N 2-Me-6-OCF(CF₃)₂ 101 III-10 CH(Me)CH═NOMe CH CH CH CH N 2-Me-6-OCF(CF₃)₂ 105 III-11 CH(Me)CH═NOMe C-I CH CH CH N 2-Me-6-OCF(CF₃)₂ 160 III-12 CH(Me)CONHEt CH CH CH CH N 2-Me-6-CF(CF₃)₂ III-13 CH(Me)CON(Et)₂ CH CH CH CH N 2-Me-6-CF(CF₃)₂ III-14 C(Me)₂CH═NOH CH CH CH CH N 2-Me-6-CF(CF₃)₂ 208 III-15 C(Me)₂CH═NOMe CH CH CH CH N 2-Me-6-CF(CF₃)₂ 162 III-16 C(Me)₂CH═NOMe C-I CH CH CH N 2-Me-6-CF(CF₃)₂ III-17 CH(Me)CONHEt CH CH CH CH N 2-Me-6-CF(CF₃)₂ III-18 CH(Me)CON(Et)₂ CH CH CH CH N 2-Me-6-CF(CF₃)₂ III-19 CH(Me)C(═O)H CH CH CH CH N 2-Me-6-CF(CF₃)₂ III-20 CH(Me)CH═NOH CH CH CH CH N 2-Me-6-CF(CF₃)₂ III-21 CH(Me)CH═NOMe CH CH CH CH N 2-Me-6-CF(CF₃)₂ III-22 CH(Me)CH═NOMe C-I CH CH CH N 2-Me-6-CF(CF₃)₂ III-23 CH(Me)CONHEt N CH CH CH CH 2-Me-4-CF(CF₃)₂ III-24 CH(Me)CH═NOMe N CH CH CH CH 2-Me-4-CF(CF₃)₂ III-25 CH(Me)CON(Et)₂ CH N CH CH CH 2-Me-4-CF(CF₃)₂ III-26 CH(Me)CH═NOMe CH N CH CH CH 2-Me-4-CF(CF₃)₂ 180 III-27 CH(Me)CONHEt CH CH N CH CH 2-Me-4-CF(CF₃)₂ III-28 CH(Me)CH═NOMe CH CH N CH CH 2-Me-4-CF(CF₃)₂ III-29 CH(Me)CON(Et)₂ CH CH CH N CH 2-Me-4-CF(CF₃)₂ III-30 CH(Me)CH═NOMe CH CH CH N CH 2-Me-4-CF(CF₃)₂ 153 III-31 CH(Me)CH═NOMe N CH N CH CH 2-Me-4-CF(CF₃)₂ III-32 CH(Me)CH═NOMe CH N CH N CH 2-Me-4-CF(CF₃)₂ III-33 CH(Me)CON(Et)₂ CH CH N CH N 2-Me-6-OCF(CF₃)₂ III-34 CH(Me)CH═NOMe CH CH N CH N 2-Me-6-OCF(CF₃)₂ III-35 CH(Me)CON(Et)₂ CH CH N CH N 2-Me-6-CF(CF₃)₂ III-36 CH(Me)CH═NOMe₂ CH CH N CH N 2-Me-6-CF(CF₃)₂ Note: In the Table 3, when Q⁵ represents nitrogen atom, then said nitrogen atom is 1-position and the substituted position of Ym is determined thereby.

The agrohorticultural composition, particularly, agrohorticultural insecticides containing the aromatic diamide derivative represented by the formula (I) or salt thereof of the present invention as an active ingredient are suitable for controlling various insect pests such as agrohorticultural insect pests, stored grain insect pests, sanitary insect pests, nematodes, etc., which are injurious to paddy rice, fruit trees, vegetables, other crops, flowers, ornamental plants, etc. They have a marked insecticidal effect, for example, on LEPIDOPTERA including summer fruit tortrix (Adoxophes orana fasciata), smaller tea tortrix (Adoxophyes sp.), Manchurian fruit moth (Grapholita inopinata), oriental fruit moth (Grapholita molesta), soybean pod border (Leguminovora glycinivorella), mulberry leafroller (Olethreutes mori), tea leafroller (Caloptilia thevivnra), Caloptilia sp.(Caloptilia zachrysa), apple leafminer (Phyllonorycter ringoniella), pear barkminer (Spulerrina astaurota), common white (Piers rapae crucivora), tobacco budworm (Heliothis sp.), codling moth (Laspey resia pomonella), diamondback moth (Plutella xylstella), apple fruit moth (Argyresthia conjugella), peach fruit moth (Carposina niponensis), rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis) tobacco moth (Ephestia elutella), mulberry pyralid (Glyphodes pyloalis), yellow rice borer (Scirpophaga incertula), rice skipper (Parnara guttata), rice armyworm (Pseudaletia separata), pink borer (Sesamia inferens), common cutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), etc.; HEMIPTERA including aster leafhopper (Macrosteles fascifrons), green rice leafhopper (Nephotettix cinctlcepts), brown rice planthopper (Nilaparvata Iugens), whitebacked rice planthopper (Sogatella furcifera), citrus psylla (Diaphorina citri), grape whitefly (Aleurolitbus tanha), sweetpotato whitefly (Bemisia tahaci), greenhouse whitefly (Trialeurodes vaporariortum), turnup aphid (Lipaphis erysimi), green peach aphid (Myzus persicae), Indian wax scale (Ceroplastes ceriferus), cottony citrus scale (Pulvinarid aurantii), camphor scale (Pseudaonidia duplex), san Jose scale (Comstockaspis perniciosa), arrowhead scale (Unapsis yanonensis), etc.; TYLENCHIDA including soybean beetle (Anomala rufocuprea), Japanese beetle (Popillia japonica), tobacco beetle (Lasioderma serricorne), powderpost beetle (Lyctus brunneus), twenty-eight-spotted ladybird (Epilachna vigintiotopunctata), azuki bean weevil (Callosohruchus chinensis) vegetable weevil (Listroderes costirostris), maize weevil (Sitophilus zeamais), boll weevil (Anthonomus gradis gradis), rice water weevil (Lissorhoptrus oryzophilus), cucurbit leaf beetle (Aulacophora femoralis), rice leaf beetle (Oulema oryzae), striped flea beetle (Phyllotreta striolata), pine shoot beetle (Tomicus piniperda), Colorado potato beetle (Leptinotarsa decemlineata), Mexican bean beetle (Epilachna varivestis), corn rootworm (Diabrotica sp.), etc.; DIPTERA including (Dacus(Zeugodacus)cticirbitae), oriental fruit fly (Dacus(Bactrocera)dorsalis), rice leafminer (Agnomyza oryzae), onion maggot (Delia antiquia), seedcorn maggot (Delia platura), soybean pod gall midge (Asphondylia sp.), muscid fly (Musca domestica), house mosquito (Culex pipiens pipiens), etc.; and TYLENCHIDA including root-lesion nematode (Pratylenchus sp.), coffee root-lesion nematode (Pratylenchus coffeae), potato cyst nematode (Globodera rostochiensis), root-knot nematode (Meloidogyne sp.), citrus nematode (Tylenchulus semipenetrans), Aphelenchus sp. (Aphelenchus avenae), chrysanthemum foliar (Aphelenchoides ritzemabosi), etc.

The agrohorticultural composition, particularly, agrohorticultural insecticides containing the aromatic diamide derivative represented by formula (I) or salt thereof of the present invention has a marked controlling effect on the above-exemplified insect pests, sanitary pests and/or nematodes, which are injurious to paddy field crops, upland crops, fruit trees, vegetables and other crops, flowers and ornament plants, and the like. Therefore, the desired effect of the agrohorticultural insecticide of the present invention can be exhibited by applying the insecticide to the paddy field water, stalks and leaves or soil of paddy field, upland field, fruit trees, vegetables, other crops or flowers and ornament plants at a season at which the insect pests, sanitary pests or nematodes are expected to appear, before their appearance or at the time when their appearance is confirmed.

In general, the agrohorticultural composition of the present invention is used after being prepared into conveniently usable forms according to ordinary manner for preparation of agrochemicals.

That is, the aromatic diamide derivative of formula (I) or salt thereof and an appropriate carrier are blended optionally together with an adjuvant in a proper proportion and prepared into a suitable preparation form such as suspension, emulsifiable concentrate, soluble concentrate, wettable powder, granules, dust or tablets through dissolution, separation, suspension, mixing, impregnation, adsorption or sticking.

The inert carrier used in the present invention may be either solid or liquid. As the solid carrier, soybean flour, cereal flour, wood flour, bark flour, saw dust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose, extraction residues of vegetables, powdered synthetic polymers or resins, clay (e.g. kaolin, bentonite and acid clay), talc (e.g. talc and pyrophyllite), silica materials (e.g. diatomaceous earth, siliceous sand, mica, white carbon, i.e. synthetic high-dispersion silicic acid, also called finely divided hydrated silica or hydrated silicic acid, some of the commercially available products contain calcium silicate as the major component), activated carbon, powdered sulfur, pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic or mineral powders, chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride and the like, and compost. These carriers may be used either alone or as a mixture of two or more carriers.

The liquid carrier is that which itself has a solubility or which is without such solubility but is capable of dispersing an active ingredient with the aid of an adjuvant. The following are typical examples of the liquid carrier and can be used alone or as a mixture thereof. Water; alcohols such as methanol, ethanol, isopropanol, butanol and ethylene glycol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone; ethers such as ethyl ether, dioxane, cellosolve, dipropyl ether and tetrahydrofuran; aliphatic hydrocarbons such as kerosene and mineral oil; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalene; halogenated hydrocarbons such as dichlorethane, chloroform, carbon tetrachloride and chlorobenzene; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate; amides such as dimethylformamide, diethylformamide and dimethylacetamide; nitrites such as acetonitrile; and dimethyl sulfoxide.

The following are typical examples of the adjuvant, which are used depending upon purposes and used alone or in combination of two or more adjuvants in some cases, or need not to be used at all.

To emulsify, disperse, dissolve and/or wet an active ingredient, a surfactant is used. As the surfactant, there can be exemplified polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resinates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalene-sulfonic acid condensation products, ligninsulfonates and higher alcohol sulfate esters.

Further, to stabilize the dispersion of an active ingredient, tackify it and/or bind it, there may be used adjuvants such as casein, gelatin, starch, 20, methyl cellulose, carboxymethyl cellulose, gum arabic, polyvinyl alcohols, turpentine, bran oil, bentonite and ligninsulfonates.

To improve the flowability of a solid product, there may be used adjuvants such as waxes, stearates and alkyl phosphates.

Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for dispersible products.

Adjuvants such as silicone oil may also be used as a defoaming agent.

The content of the active ingredient may be varied according to the need. For example, in dusts or granules, the suitable content thereof is from 0.01 to 50% by weight. In emulsifiable concentrate and flowable wettable powder, too, the suitable content is from 0.01 to 50% by weight.

The agrohorticultural composition, particularly agrohorticultural insecticide of the present invention is used to control a variety of insect pests in the following manner. That is, it is applied to a crop on which the insect pests are expected to appear or a site where appearance of the insect pests is undesirable, as it is or after being properly diluted with or suspended in water or the like, in an amount effective for control of the insect pests.

The agrohorticultural composition, particularly the agrohorticultural insecticide of the present invention can also be used to, for example, seeds of plants to be protected from pests, or to cultivation carriers in which the above seeds are to be sown (e.g. sowing soil, nursery mat, water, etc.); and can be used by a method such as application to rice nursery bed, seed dressing, seed disinfection or the like. When applied to pests which verminate in upland crops such as fruit trees, grains, vegetables and the like, it can be used by seed treatments such as dressing, soaking and the like, or by drenching or surface spraying/watering to, for example, seedling-raising carriers such as cultivation vessel, planting hole and the like to allow the crops to absorb the present insecticide, or by application to water culture solution for water culture.

The applying dosage of the agrohorticultural composition of the present invention is varied depending upon various factors such as a purpose, insect pests to be controlled, a growth state of a plant, tendency of insect pests appearance, weather, environmental conditions, a preparation form, an application method, an application site and an application time. It may be properly chosen in a range of 0.1 g to 10 kg (in terms of active ingredient compound) per 10 ares depending upon purposes.

The agrohorticultural composition of the present invention may be used in admixture with other agricultural and horticultural disease or pest controllers in order to expand both spectrum of controllable diseases and insect pest species and the period of time when effective applications are possible or to reduce the dosage.

Next, typical examples and test examples of the invention are presented below. The present invention is by no means limited by these examples.

EXAMPLES

Representative examples of the present invention are shown below. However, the present invention is not restricted to these examples.

Example 1

(1-1) Production of 3-iodo-1-N-(4-heptafluoro-isopropyl-2-methylphenyl)-phthalamic acid

A solution of 3.5 g of 4-heptafluoro-isopropyl-2-methylaniline dissolved in 3 ml of acetonitrile was dropwise added slowly to a suspension of 3.5 g of 3-iodophthalic anhydride suspended in 30 ml of acetonitrile, with ice-cooling. After the completion of the dropwise addition, a reaction was conducted for 3 hours at room temperature, with stirring. After the completion of the reaction, the precipitated crystals were collected by filtration and washed with a small amount of acetonitrile to obtain 4.0 g of an intended compound.

Physical property: melting point=174-181° C.

Yield: 57%

(1-2) Production of 3-iodo-N-(4-heptafluoroisopropyl-2-methylphenyl)phthalisoimide

1.1 g of trifluoroacetic anhydride was added to a suspension of 2.0 g of 3-iodo-1-N-(4-hepta-fluoroisopropyl-2-methylphenyl)-phthalamic acid suspended in 10 ml of toluene. A reaction was conducted at room temperature for 30 minutes, with stirring. After the completion of the reaction, the solvent was removed by vacuum distillation to obtain 2.0 g of a crude intended compound. The compound was used in the next reaction without being purified.

¹H-NMR [CDCl₃/TMS, δ(ppm)]

2.4 (3H,s), 7.3 (1H,d), 7.4 (2H,m), 7.5

(1H,t), 8.1 (1H,d), 8.2 (1H,d)

(1-3) Production of 3-iodo-N¹-(4-heptafluoroisopropyl-2-methylphenyl)-N²-[1-methyl-2-(N,N-dimethylcarbamoyl)-ethyl]phthalamide (compound No. 77)

1.0 g of 3-iodo-N-(4-heptafluoroisopropyl-2-methylphenyl) phthalisoimide was dissolved in 10 ml of acetonitrile. To the resulting solution were added 0.35 g of 3-amino-N,N-dimethylbutyramide hydrochloride and 0.21 g of triethylamine. The resulting mixture was stirred at room temperature for 10 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was removed by vacuum distillation, and the resulting residue was purified by silica gel column chromatography to obtain 0.4 g of an intended product.

Physical property: melting point=126° C.

Yield: 32%

Example 2 Production of 3-iodo-N¹-(4-heptafluoro-isopropyl-2-methylphenyl)-N²-[1-methyl-2-(methoxyimino)-ethyl]phthalamide (compound No. 136)

0.9 g of 3-iodo-N-(4-heptafluoroisopropyl-2-methylphenyl)phthalisoimide was dissolved in 10 ml of acetonitrile. To the resulting solution were added 0.34 g of 1-methyl-2-(methoxyimino)ethylamine hydrochloride and 0.25 g of triethylamine. The resulting mixture was stirred at room temperature for 10 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was removed by vacuum distillation, and the resulting residue was purified by silica gel column chromatography to obtain 0.36 g of an intended product.

Physical property: melting point=192° C.

Yield: 36%

Example 3

(3-1) Production of 3-iodo-2-N-[1-methyl-2-(ethoxycarbonyl)ethyl]-phthalamic acid

A solution of 1.4 g of ethyl 3-aminobutyrate dissolved in 3 ml of acetonitrile was dropwise added slowly to a suspension of 2.7 g of 3-iodophthalic anhydride suspended in 30 ml of acetonitrile, with ice-cooling. After the completion of the dropwise addition, a reaction was conducted for 3 hours at room temperature, with stirring. After the completion of the reaction, the precipitated crystals were collected by filtration and washed with a small amount of acetonitrile to obtain 3.8 g of an intended compound.

Yield: 97%

(3-2) Production of 6-iodo-N-[1-methyl-2-(ethoxycarbonyl)ethyl]phthalisoimide

1.1 g of trifluoroacetic anhydride was added to a suspension of 1.0 g of 3-iodo-2-N-[1-methyl-2-(ethoxycarbonyl)ethyl]phthalamic acid suspended in 10 ml of toluene. A reaction was conducted at room temperature for 30 minutes, with stirring. After the completion of the reaction, the solvent was removed by vacuum distillation to obtain 0.9 g of a crude intended compound. The compound was used in the next reaction without being purified.

(3-3) Production of 3-iodo-N′-(4-heptafluoroisopropyl-2-methylphenyl)-N-2-[1-methyl-2-(ethoxycarbonyl)-ethyl]phthalamide (compound No. 11)

0.90 g of 6-iodo-N-[1-methyl-2-(ethoxycarbonyl)ethyl]phthalisoimide was dissolved in 10 ml of acetonitrile. To the resulting solution were added 0.5 g of 4-heptafluoroisopropyl-2-methylaniline and two drops of trifluoroacetic acid. The resulting mixture was stirred at room temperature for 10 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was removed by vacuum distillation, and the resulting residue was purified by silica gel column chromatography to obtain 0.50 g of an intended product.

Physical property: paste-like

Yield: 31%

¹H-NMR [CDCl₃/TMS, δ(ppm)]

1.1-1.4 (5H,m), 2.4 (3H,s), 2.5-2.6 (2H,m),

4.1 (2H,q), 4.4-4.5 (1H,m), 6.8 (1H,d), 7.2

(1H,t), 7.4-7.5 (2H,m), 7.8 (1H,d), 7.9

(1H,d), 8.3 (1H,d), 8.5 (1H,s)

Example 4 Production of 3-iodo-N¹-(4-heptafluoro-isopropyl-2-methylphenyl)-N²-(3-oxobutan-2-yl)-phthalamide (compound No. 134)

1.5 g of 3-iodo-N-(4-heptafluoroisopropyl-2-methylphenyl)phthalisoimide was dissolved in 10 ml of acetonitrile. To the resulting solution were added 0.35 g of 3-aminobutanone hydrochloride and 0.29 g of triethylamine. The resulting mixture was stirred at room temperature for 10 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into ice water, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was removed by vacuum distillation, and the resulting residue was purified by silica gel column chromatography to obtain 0.70 g of an intended product.

Physical property: melting point=189° C.

Yield: 41%

Next, typical formulation examples and test examples of the invention are presented below. The present invention is by no means limited by these examples.

In the formulation examples, the term “parts” means “parts by weight”.

Formulation Example 1

Each compound listed in Tables 1 to 3 50 parts Xylene 40 parts Mixture of polyoxyethylene nonylphenyl 10 parts ether and calcium alkylbenzenesulfonate

An emulsifiable concentrate was prepared by mixing uniformly the above ingredients to effect dissolution.

Formulation Example 2

Each compound listed in Tables 1 to 3  3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts

A dust was prepared by mixing uniformly and grinding the above ingredients.

Formulation Example 3

Each compound listed in Tables 1 to 3  5 parts Mixed powder of bentonite and clay 90 parts Calcium ligninsulfonate  5 parts

Granules were prepared by mixing the above ingredients uniformly, and kneading the resulting mixture together with a suitable amount of water, followed by granulation and drying.

Formulation Example 4

Each compound listed in Tables 1 to 3 20 parts Mixture of kaolin and synthetic 75 parts high-dispersion silicic acid Mixture of polyoxyethylene nonylphenyl  5 parts ether and calcium alkylbenzenesulfonate

A wettable powder was prepared by mixing uniformly and grinding the above ingredients.

Formulation Example 5

Each compound listed in Tables 1 to 3 20 parts Sodium alkylnapthalenesulfonate 3 parts Propylene glycol 5 parts Dimethylpolysiloxane 0.25 part p-Chloro-m-xylenol 0.10 part Xanthan gum 0.30 part Water 71.35 part

A wettable powder or wettable suspension was prepared by mixing uniformly and wet-grinding the above ingredients.

Test Example 1 Insecticidal Effect on Diamond Back Moth (Pluitepla xylostellg)

Adult diamond back moths were released and allowed to oviposit on a Chinese cabbage seedling. Two days after the release, the seedling having the eggs deposited thereon was immersed for about 30 seconds in a liquid chemical prepared by diluting a preparation containing each compound listed in Tables 1 to 3 as an active ingredient to adjust the concentration to 50 ppm. After air-dryness, it was allowed to stand in a room thermostatted at 25° C. Six days after the immersion, the hatched insects were counted. The mortality was calculated according to the following equation and the insecticidal effect was judged according to the criterion shown below. The test was carried out with triplicate groups of 10 insects. $\begin{matrix} {Corrected} \\ {{mortality}\quad(\%)} \end{matrix} = {\frac{\begin{matrix} {{{Number}\quad{of}\quad{hatched}\quad{insects}\quad{in}\quad{untreated}\quad{group}} -} \\ {{Number}\quad{of}\quad{hatched}\quad{insects}\quad{in}\quad{treated}\quad{group}} \end{matrix}}{{Number}\quad{of}\quad{hatched}\quad{insects}\quad{in}\quad{untreated}\quad{group}} \times 100.}$ Criterion:

-   -   A—Mortality 100%     -   B—Mortality 99-90%     -   C—Mortality 89-80%     -   D—Mortality 79-50%

Test Example 2 Insecticidal Effect on Common Cutworm (Spodoptera litura)

A piece of cabbage leaf (cultivar; Shikidori) was immersed for about 30 seconds in a liquid chemical prepared by diluting a preparation containing each compound listed in Tables 1 to 3 as an active ingredient to adjust the concentration to 500 ppm. After air-dryness, it was placed in a plastic Petri dish with a diameter of 9 cm and inoculated with second-instar larvae of common cutworm, after which the dish was closed and then allowed to stand in a room thermostatted at 25° C. Eight days after the inoculation, the dead and alive were counted. The mortality was calculated according to the following equation and the insecticidal effect was judged according to the criterion shown in Test Example 1. The test was carried out with triplicate groups of 10 insects. $\begin{matrix} {Corrected} \\ {{mortality}\quad(\%)} \end{matrix} = {\frac{\begin{matrix} {{{Number}\quad{of}\quad{alive}\quad{larvae}\quad{in}\quad{untreated}\quad{group}} -} \\ {{Number}\quad{of}\quad{alive}\quad{larvae}\quad{in}\quad{treated}\quad{group}} \end{matrix}}{{Number}\quad{of}\quad{alive}\quad{larvae}\quad{in}\quad{untreated}\quad{group}} \times 100}$

Test Example 3 Insecticidal Effect on Smaller Tea Tortrix (Adxophyes sp.)

Tea leaves were immersed for about 30 seconds in a liquid chemical prepared by diluting a preparation containing each compound listed in Tables 1 to 3 as an active ingredient to adjust the concentration to 50 ppm. After air-dryness, the tea leaves were placed in a plastic Petri dish with a diameter of 9 cm and inoculated with larvae of smaller tea tortrix, after which the dish was allowed to stand in a room thermostatted at 259 and having a humidity of 70%. Eight days after the inoculation, the dead and alive were counted and the insecticidal effect was judged according to the criterion shown in Test Example 1. The test was carried out with triplicate groups of 10 insects.

In the test mentioned above, the compounds which exhibited an activity ranking B or higher against diamond back moth (Pluitella xyvlstplla) were as follows:

2˜11, 70˜78, 134, 136˜141, 177, 204, 205, 207, 215˜219, 226, 229, 230˜237, 239, 241˜296, 298, 302, 304, 306, 309, III-3, III-5, III-91˜II-11, III-14, III-15, III-26 and III-30.

Further, the compounds which exhibited an activity ranking B or higher against Common cutworm (Spodoptera litura) were as follows:

11, 71˜74, 77, 78, 136˜140, 204, 205, 207, 216, 226, 246, 248, 256, 258, 260, 263, 265, 272, 275, 277˜279, 284˜286, 291, 292, 309, III-3, III-5 and III-11.

Furthermore, the compounds which exhibited an activity ranking B or higher against smaller tea tortrix (Adxophyes sp.) were as follows:

7, 11, 70˜72, 74˜78, 134, 136˜140, 204, 205, 207, 216, 218, 219, 226, 246˜250, 253, 254, 256, 258, 259, 263, 265, 266, 271˜273, 275˜279, 281, 283, 285, 286, 290, 291, 296, 298, 304, 309, III-3, III-5, III-10, III-11, III-15 and III-26. 

1. An aromatic diamide compound represented by the following general formula (I) or a salt thereof:

{wherein A¹ is a (C₁-C₈)alkylene group; a substituted (C₁-C₈) alkylene group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₅)alkylsulfonyl groups, (C₁-C₆)alkylthio(C₁-C₆)alkyl groups, (C₁-C₆)-alkoxycarbonyl groups and phenyl group; a (C₃-C₈)-alkenylene group; a substituted (C₃-C₈)alkenylene group having one or more same or different subsbtuents selected from halogen atoms, cyano group, nitro group, halo(C₁-C₈)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, (C₁-C₆)-alkylthio(C₁-C₆)alkyl groups, (C₁-C₆)alkoxycarbonyl groups and phenyl group; a (C₃-C₈)alkynylene group; or a substituted (C₃-C₈)alkynylene group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)-alkylthio groups, halo( C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, (C₁-C₆)alkylthio(C₁-C₆)alkyl groups, (C₁-C₆)alkoxycarbonyl groups and phenyl group; in the (C₁-C₈)alkylene group, the substituted (C₁-C₈) alkylene group, the (C₃-C₈)alkenylene group, the substituted (C₃-C₈) alkenylene group, the (C₃-C₈)-alkynylene group or the substituted (C₃-C₈)alkynylene group, any saturated carbon atom may be substituted with a (C₂-C₅)alkylene group to form a (C₃-C₆)cycloalkane ring; further in the (C₁-C₆)alkylene group, the substituted (C₁-C₈) alkylene group, the (C₃-C₈)alkenylene group or the substituted (C₃-C₈) alkenylene group, any two carbon atoms may be combined with an alkylene group or an alkenylene group to form a (C₃-C₆)cycloalkane ring or a (C₃-C₆)cycloalkene ring; B is —C(═N—OR⁴)— (wherein R⁴ is a hydrogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl group; a halo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynyl group; a (C₃-C₆)cycloalkyl group; a phenyl(C₁-C₄)alkyl group; or a substituted phenyl(C₁-C₄)alkyl group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups); R¹ is a hydrogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₂-C₆)alkenyl group; a halo(C₂-C₆)alkenyl group; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxy group; a halo(C₁-C₆)alkoxy group; a (C₁-C₆)alkylthio group; a halo(C₁-C₆)alkylthio group; a mono(C₁-C₆)alkylamino group; a di(C₁-C₆)alkylamino group wherein the two alkyl groups may be the same or different; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a phenylamino group; a substituted phenylamino group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a phenyloxy group; a substituted phenyloxy group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a phenylthio group; a substituted phenylthio group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; R¹ may bond with A¹ to form a 4- to 7-membered ring which may contain, as a ring-constituting atom(s), one or two same or different atoms selected from oxygen, sulfur and nitrogen atoms; R² and R³ may be the same or different and are each a hydrogen atom, a (C₃-C₆)cycloalkyl group or —A²—R⁵ [wherein A² is —C(═O)—, —C(═S)—, —C(═NR⁶)— (wherein R⁶ is a hydrogen atom; a (C₁-C₆)alkyl group; a (C₁-C₆)alkoxy group; a mono(C₁-C₆)alkylamino group; a di(C₁-C₆)-alkylamino group wherein the two alkyl groups may be the same or different; a (C₁-C₆)alkoxycarbonyl group; a phenyl group; or a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups), a (C₁-C₈)alkylene group, a halo(C₁-C₈)alkylene group, a (C₃-C₆)alkenylene group, a halo(C₃-C₆)alkenylene group, a (C₃-C₆)alkynylene group or a halo(C₃-C₆)alkynylene group; (1) when A² is —C(═O)—, —C(═S)— or —C(═NR⁶)— (wherein R⁶ has the same definition as given above), R⁵ is a hydrogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)-alkyl group; a (C₁-C₆)alkoxy group; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; or —A³—R⁷ (wherein A³ is —O—, —S— or —N(R⁸)— (wherein R⁸ is a hydrogen atom; a (C₁-C₆)-alkylcarbonyl group; a halo(C₁-C₆)alkylcarbonyl group; a (C₁-C₆)alkoxycarbonyl group; a phenylcarbonyl group; a substituted phenylcarbonyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)-alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a phenyl(C₁-C₄)alkoxycarbonyl group; or a substituted phenyl(C₁-C₄)alkoxycarbonyl group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₅)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups); and R⁷ is a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl group; a halo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynyl group; a halo(C₃-C₆)alkynyl group; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkylcarbonyl group; a halo(C₁-C₆)alkylcarbonyl group; a (C₁-C₆)-alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a phenyl(C₁-C₄)alkyl group; a substituted phenyl(C₁-C₄)alkyl group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₈)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups); (2) when A² is a (C₁-C₈)alkylene group, a halo(C₁-C₈)alkylene group, a (C₃-C₆)alkenylene group, a halo(C₃-C₆)alkenylene group, a (C₃-C₆)alkynylene group or a halo(C₃-C₆)alkynylene group, R⁵ is a hydrogen atom; a halogen atom; a cyano group; a nitro group; a (C₃-C₆)-Cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; or —A⁴—R⁹ —(wherein A⁴ is —O—, —S—, —SO—, —SO₂—, —N(R⁸)— (R⁸ has the same definition as given above), —C(═O)— or —C(═NOR⁴)— (R⁴ has the same definition as given above); (i) when A⁴ is —O—, —S—, —SO—, —SO₂— or —N(R⁸)— (R⁸ has the same definition as given above), R⁹ is a hydrogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl group; a halo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynyl group; a halo(C₃-C₆)alkynyl group; a (C₃C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkylcarbonyl group; a halo(C₁-C₆)-alkylcarbonyl group; a (C₁-C₆)alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a phenyl(C₁-C₄)alkyl group; a substituted phenyl(C₁-C₄)alkyl group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₈)alkyl groups, (C₁-C₆) alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)-alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; (ii) when A⁴ is —C(═O)— or —C(═N—OR⁴)— (R⁴ has the same definition as given above), R⁹ is a hydrogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₂-C₆)alkenyl group; a halo(C₂-C₆)alkenyl group; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxy group; a halo(C₁-C₆)alkoxy group; a (C₁-C₆)alkylthio group; a halo(C₁-C₆)alkylthio group; a mono(C₁-C₆)alkylamino group; a di(C₁-C₆)alkylamino group wherein the two alkyl groups may be the same or different; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)-alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a phenylamino group; a substituted phenylamino group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a phenyloxy group; a substituted phenyloxy group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a phenylthio group; a substituted phenylthio group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups)]; R² may bond with A¹ or R¹ to form a 4- to 7-membered ring which may contain, as a ring-constituting atom(s), one or two same or different atoms selected from oxygen, sulfur and nitrogen atoms; Q¹ to Q⁴ are each a carbon atom which may be substituted with X, and X may be the same or different, and is a halogen atom; a cyano group; a nitro group; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; or —A⁵—R¹⁰ [wherein A⁵ is —O—, —S—, —SO—, —SO₂—, —C(═O)—, —C(═NOR⁴) (R⁴ has the same definition as given above), a (C₁-C₆)alkylene group, a halo(C₁-C₆)alkylene group, a (C₂-C₆)alkenylene group, a halo(C₂-C₆)alkenylene group, a C₂-C₆)alkynylene group or a halo(C₂-C₆)alkynylene group; (1) when A⁵ is —O—, —S—, —SO— or —SO₂—, R¹⁰ is a halo(C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkenyl group; a phenyl group; a substituted phenyl group having one or more same or different subsbtuents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)-alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)-alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; or —A⁶—R¹¹ (wherein A⁶ is a (C₁-C₆)alkylene group, a halo(C₁-C₆)-alkylene group, a (C₃-C₆)alkenylene group, a halo(C₃-C₆)-alkenylene group, a (C₃-C₆)alkynylene group or a halo(C₃-C₆)alkynylene group, and R¹¹ is a hydrogen atom; a halogen atom; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)-cycloalkyl group; a (C₁-C₆)alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; or —A⁷—R¹² (wherein A⁷ is —O—, —S—, —SO— or —SO₂—, and R¹² is a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl group; a halo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynyl group; a halo(C₃-C₆)alkynyl group; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups)); (2) when A⁵ is —C(═O)— or —C(═NOR⁴)— (R⁴ has the same definition as given above), R¹⁰ is a (C₁-C₆)-alkyl group; a halo(C₁-C₆)alkyl group; a (C₂-C₆)alkenyl group; a halo(C₂-C₆)alkenyl group; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxy group; a (C₁-C₆)alkylthio group; a mono(C₁-C₆)alkylamino group; a di(C₁-C₆)alkylamino group wherein the two alkyl groups may be the same or different; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a phenylamino group; a substituted phenylamino group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)-alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; (3) when A⁵ is a (C₁-C₆)alkylene group, a halo(C₁-C₆)alkylene group, a (C₂-C₆)alkenylene group, a halo(C₂-C₆)alkenylene group, a (C₂-C₆)alkynylene group or a halo(C₂-C₆)alkynylene group, R¹⁰ is a hydrogen atom; a halogen atom; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxycarbonyl group; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; or —A⁸—R¹³ (wherein A⁸ is —O—, —S—, —SO— or —SO₂—, and R¹³ is a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cydoalkyl group; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; or —A⁹—R¹⁴ (wherein A⁹ is a (C₁-C₆)alkylene group, a halo(C₁-C₆)alkylene group, a (C₂ -C₆)alkenylene group, a halo(C₂-C₆)alkenylene group, a (C₂-C₆)alkynylene group or a halo(C₃-C₅)alkynylene group, and R¹⁴ is a hydrogen atom; a halogen atom; a (C₃-C₆)Cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxy group; a halo(C₁-C₆)alkoxy group; a (C₁-C₆)alkylthio group; a halo(C₁-C₆)alkylthio group; a (C₁-C₆)alkylsulfinyl group; a halo(C₁-C₆)alkylsulfinyl group; a (C₁-C₆)alkylsulfonyl group; a halo(C₁-C₆)alkylsulfonyl group; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)-alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)-alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a phenyloxy group; a substituted phenyloxy group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₅)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)-alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a phenylthio group; a substituted phenylthio group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups))]; the two Xs bonding to the adjacent two carbon atoms constituting the aromatic ring containing Q¹ to Q⁴ may bond to each other to form a condensed ring; the condensed ring may have one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)-alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; Q⁵ is a nitrogen atom or a carbon atom; Y may be the same or different, and is a halogen atom; a cyano group; a nitro group; a halo(C₃-C₆)cycloalkyl group; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)-alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-Cr)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)-alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; or —A⁵—R¹⁰ (A⁵ and R¹⁰ each have the same definition as given above); the two Ys bonding to the adjacent two carbon atoms constituting the aromatic ring containing Q⁵ may bond to each other to form a condensed ring; the condensed ring may have one or more same or different substituents selected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, phenyl group, substituted phenyl groups having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups, heterocyclic groups, and substituted heterocyclic groups having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; m is an integer of 0 to 5; Z¹ and Z² may be the same or different and are each an oxygen atom or a sulfur atom.
 2. An aromatic diamide compound or a salt thereof according to claim 1, wherein A¹ is a (C₁-C₈)alkylene group; a substituted (C₁-C₈) alkylene group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, halo(C₁-C₆)alkyl groups, (C₁-C₈)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, (C₁-C₅)alkylthio(C₁-C₆)alkyl groups, (C₁-C₆)alkoxycarbonyl groups and phenyl group; a (C₃-C₈)alkenylene group; a substituted (C₃-C₈)alkenylene group having one or more same or different substituents selected form halogen atoms, cyano group, nitro group, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)-alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, (C₁-C₆)alkylthio(C₁-C₆)alkyl groups, (C₁-C₆)alkoxycarbonyl groups and phenyl group; a (C₃-C₈)alkynylene group; or a substituted (C₃-C₈)alkynylene group having one or more same or different substituents selected form halogen atoms, cyano group, nitro group, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)-alkylsulfonyl groups, (C₁-C₆)alkylthio(C₁-C₆)alkyl groups, (C₁-C₆)alkoxycarbonyl groups and phenyl group; in the (C₁-C₈)alkylene group, the substituted (C₁-C₈)alkylene group, the (C₃-C₈)alkenylene group, the substituted (C₃-C₈)alkenylene group, the (C₃-C₈)-alkynylene group or the substituted (C₃-C₈)alkynylene group, any saturated carbon atom may be substituted with a (C₂-C₅)alkylene group to form a (C₃-C₆)cycloalkane ring; further in the (C₁-C₈)alkylene group, the substituted (C₁-C₈) alkylene group, the (C₃-CB)alkenylene group or the substituted (C₃-C₈) alkenylene group, any two carbon atoms may be combined with an alkylene group or an alkenylene group to form a (C₃-C₆)cycloalkane ring or a (C₃-C₆)cycloalkene ring; B is —C(═N—OR⁴)— (wherein R⁴ is a hydrogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl group; a halo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynyl group; a (C₃-C₆)cycloalkyl group; a phenyl(C₁-C₄)alkyl group; or a substituted phenyl(C₁-C₄)alkyl group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups); R¹ is a hydrogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₂-C₆)alkenyl group; a halo(C₂-C₆)alkenyl group; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxy group; a halo(C₁-C₆)alkoxy group; a (C₁-C₆)alkylthio group; a halo(C₁-C₆)alkylthio group; a mono(C₁-C₆)alkylamino group; a di(C₁-C₆)alkylamino group wherein the two alkyl groups may be the same or different; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a phenylamino group; a substituted phenylamino group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₈)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-Ce)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)-alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a phenyloxy group; a substituted phenyloxy group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a phenylthio group; a substituted phenylthio group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; R¹ may bond with A¹ to form a 4- to 7-membered ring which may contain, as a ring-constituting atom(s), one or two same or different atoms selected from oxygen, sulfur and nitrogen atoms; R² and R³ may be the same or different and are each a hydrogen atom or a (C₁-C₆)alkyl group; Q¹ to Q⁴ are each a carbon atom which may be substituted with X; X may be the same or different, and is a halogen atom, a nitro group, a (C₁-C₆)alkyl group, a halo(C₁-C₆)alkyl group, a (C₂C₆)alkenyl group, a halo(C₂-C₆)alkenyl group, a (C₂C₆)alkynyl group, a halo(C₂-C₆)alkynyl group, a halo(C₁-C₆)alkoxy group or a halo(C₁-C₆)alkylthio group; the two Xs bonding to the adjacent two carbon atoms constituting the aromatic ring containing Q¹ to Q⁴ may bond to each other to form a condensed ring; the condensed ring may have one or more same or different substituents selected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)-alkylsulfonyl groups; Q⁵ is a nitrogen atom or a carbon atom; Y may be the same or different when it is more than one, and is a halogen atom; a cyano group; a nitro group; a halo(C₃-C₆)cycloalkyl group; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)-alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a heterocyclic group; a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆) alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; or —A⁵—R¹⁰ (A⁵ and R¹⁰ each have the same definition as given in claim 1); the two Ys bonding to the adjacent two carbon atoms constituting the aromatic ring containing Q⁵ may bond to each other to form a condensed ring; the condensed ring may have one or more same or different substituents selected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, phenyl group, substituted phenyl groups having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups, heterocyclic groups, and substituted heterocyclic groups having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; m is an integer of 0 to 5; Z¹ and Z² are each an oxygen atom.
 3. An aromatic diamide compound or a salt thereof according to claim 2, wherein A¹ is a (C₁-C₈)-alkylene group; a substituted (C₁-C₈) alkylene group having one or more same or different substituents selected form halogen atoms, cyano group, nitro group, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-Cr)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, (C₁-C₆)-alkylthio(C₁-C₆)alkyl groups, (C₁-C₆)alkoxycarbonyl groups and phenyl group; a (C₃-C₈)alkenylene group; a substituted (C₃-C₈)alkenylene group having one or more same or different substituents selected form halogen atoms, cyano group, nitro group, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₈)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)-alkylsulfonyl groups, (C₁-C₆)alkylthio(C₁-C₆)alkyl groups, (C₁-C₆)alkoxycarbonyl groups and phenyl group; a (C₃-C₈)alkynylene group; or a substituted (C₃-C₈)alkynylene group having one or more same or different substituents selected form halogen atoms, cyano group, nitro group, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, (C₁-C₆)alkylthio(C₁-C₆)alkyl groups, (C₁-C₆)alkoxycarbonyl groups and phenyl group; in the (C₁-C₈)alkylene group, the substituted (C₁-C₈)alkylene group, the (C₃-C₈)alkenylene group, the substituted (C₃-C₈) alkenylene group, the (C₃-C₈)-alkynylene group or the substituted (C₃-C₈)alkynylene group, any saturated carbon atom may be substituted with a (C₂-C₅)alkylene group to form a (C₃-C₆)cycloalkane ring; further in the (C₁-C₈)alkylene group, the substituted (C₁-C₈) alkylene group, the (C₃-C₈)alkenylene group or the substituted (C₃-C₈) alkenylene group, any two carbon atoms may be combined with an alkylene group or an alkenylene group to form a (C₃-C₆)cycloalkane ring or a (C₃-C₆)cycloalkene ring; B is —C(═N—OR⁴)— (wherein R⁴ is a hydrogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₃-C₆)alkenyl group; a halo(C₃-C₆)alkenyl group; a (C₃-C₆)alkynyl group; a (C₃-C₆)cycloalkyl group; a phenyl(C₁-C₄)alkyl group; or a substituted phenyl(C₁-C₄)alkyl group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups); R¹ is a hydrogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₂-C₆)alkenyl group; a halo(C₂-C₆)alkenyl group; a (C₃-C₆)cycloalkyl group; a halo(C₃-C₆)cycloalkyl group; a (C₁-C₆)alkoxy group; a halo(C₁-C₆)alkoxy group; a (C₁-C₆)alkylthio group; a halo(C₁-C₆)alkylthio group; a mono(C₁-C₆)alkylamino group; a di(C₁-C₆)alkylamino group wherein the two alkyl groups may be the same or different; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a phenylamino group; a substituted phenylamino group having, on the ring, one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)-alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)alkoxycarbonyl groups; a phenyloxy group; a substituted phenyloxy group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁ -C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a phenylthio group; a substituted phenylthio group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; a heterocyclic group; or a substituted heterocyclic group having one or more same or different substituents selected from halogen atoms, cyano group, nitro group, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)-alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups, halo(C₁-C₆)alkylsulfonyl groups, mono(C₁-C₆)alkylamino groups, di(C₁-C₆)alkylamino groups wherein the two alkyl groups may be the same or different, and (C₁-C₆)-alkoxycarbonyl groups; R¹ may bond with A¹ to form a 4- to 7-membered ring which may contain, as a ring-constituting atom(s), one or two same or different atoms selected from oxygen, sulfur and nitrogen atoms; R² and R³ may be the same or different and are each a hydrogen atom or a (C₁-C₆)alkyl group; Q¹ to Q⁴ are each a carbon atom which may be substituted with X; X may be the same or different when it is more than one, and is a halogen atom, a nitro group, a (C₁-C₆)alkyl group, a halo(C₁-C₆)alkyl group, a (C₂-C₆)alkenyl group, a halo(C₂-C₆)alkenyl group, a (C₂-C₆)alkynyl group, a halo(C₂-C₆)alkynyl group, a halo(C₁-C₆)alkoxy group or a halo(C₁-C₆)alkylthio group; the two Xs bonding to the adjacent two carbon atoms constituting the aromatic ring containing Q¹ to Q⁴ may bond to each other to form a condensed ring; the condensed ring may have one or more same or different substituents selected from halogen atoms, (C₁-C₆)alkyl groups, halo(C₁-C₆)alkyl groups, (C₁-C₆)alkoxy groups, halo(C₁-C₆)alkoxy groups, (C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylthio groups, (C₁-C₆)alkylsulfinyl groups, halo(C₁-C₆)alkylsulfinyl groups, (C₁-C₆)alkylsulfonyl groups and halo(C₁-C₆)alkylsulfonyl groups; Q⁵ is a nitrogen atom or a carbon atom; Y may be the same or different when it is more than one, and is a halogen atom; a (C₁-C₆)alkyl group; a halo(C₁-C₆)alkyl group; a (C₁-C₆)alkoxy group; a halo(C₁-C₆)alkoxy group; a (C₁-C₆)alkylthio group; a halo(C₁-C₆)alkylthio group; a (C₁-C₆)alkylsulfinyl group; a halo(C₁-C₆)alkylsulfinyl group; a (C₁-C₆)alkylsulfonyl group; a halo(C₁-C₆)alkylsulfonyl group; a halo(C₁-C₆)alkoxy halo(C₁-C₆)alkoxy group; a phenyl group; a substituted phenyl group having one or more same or different substituents selected from halogen atoms, cyano group, halo(C₁-C₆)alkyl groups, halo(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkylthio groups, halo(C₁-C₆)-alkylsulfinyl groups and halo(C₁-C₆)alkylsulfonyl groups; a phenyloxy group; a substituted phenyloxy group having one or more same or different substituents selected from halogen atoms, cyano group, halo(C₁-C₆)-alkyl groups, halo(C₁-C₆)alkoxy groups, halo(C₁-C₆)-alkylthio groups, halo(C₁-C₆)alkylsulfinyl groups and halo(C₁-C₆)alkylsulfonyl groups; a pyridyloxy group; or a substituted pyridyloxy group having one or more same or different substituents selected from halogen atoms, cyano group, halo(C₁-C₆)alkyl groups, halo(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkylthio groups, halo(C₁-C₆)-alkylsulfinyl groups and halo(C₁-C₆)alkylsulfonyl groups; the two Ys bonding to the adjacent two carbon atoms constituting the aromatic ring containing Q⁵ may bond to each other to form a condensed ring; the condensed ring may have one or more same or different substituents selected from halogen atoms; (C₁-C₆)alkyl groups; halo(C₁-C₆)alkyl groups; (C₁-C₆)alkoxy groups; halo(C₁-C₆)alkoxy groups; (C₁-C₆)alkylthio groups; halo(C₁-C₆)alkylthio groups; (C₁-C₆)alkylsulfinyl groups; halo(C₁-C₆)alkylsulfinyl groups; (C₁-C₆)alkylsulfonyl groups; halo(C₁-C₆)alkylsulfonyl groups; phenyl group; and substituted phenyl groups having one or more same or different substituents selected from halogen atoms, halo(C₁-C₆)alkyl groups, halo(C₁-C₆)alkoxy groups, halo(C₁-C₆)alkylthio groups, halo(C₁-C₆)alkylsulfinyl groups and halo(C₁-C₆)alkylsulfonyl groups; m is an integer of 1 to 5; Z¹ and Z² are each an oxygen atom.
 4. An agrohorticultural composition characterised by containing, as an effective ingredient, an aromatic diamide compound of a salt thereof according to claim 1 and an inert carrier.
 5. A method for using an agrohorticultural composition according to claim 4, characterized by applying the agrohorticultural composition to a target crop or soil in an effective amount to protect the crop or soil from pests. 